Synergistic weed control from applications of pyridine carboxylic acid herbicides and als inhibitors

ABSTRACT

Disclosed herein are herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and (b) an acetolactate synthase (ALS) inhibitor or an agriculturally acceptable salt or ester thereof. Also disclosed herein are methods of controlling undesirable vegetation which comprise applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and (b) an acetolactate synthase (ALS) inhibitor or an agriculturally acceptable salt or ester thereof, wherein (a) and (b) are each added in an amount sufficient to provide a herbicidal effect.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims benefit of U.S. Provisional Patent ApplicationNo. 62/050,715, filed Sep. 15, 2014, which is hereby incorporated hereinby reference in its entirety.

FIELD OF THE DISCLOSURE

The present disclosure relates to herbicidal compositions comprising aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof and (b) an acetolactate synthase (ALS) inhibitor or anagriculturally acceptable salt or ester thereof. The present disclosurealso relates to methods for controlling undesirable vegetation.

BACKGROUND

Many recurring problems in agriculture involve controlling growth ofundesirable vegetation that can, for instance, inhibit crop growth. Tohelp control undesirable vegetation, researchers have produced a varietyof chemicals and chemical formulations effective in controlling suchunwanted growth. However, a continuing need exists for new compositionsand methods to control growth of undesirable vegetation.

SUMMARY OF THE DISCLOSURE

Disclosed herein are herbicidal compositions. The herbicidalcompositions can comprise a herbicidally effective amount of (a) apyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof and (b) an acetolactate synthase (ALS)inhibitor or an agriculturally acceptable salt or ester thereof. In someembodiments, (a) and (b) can be provided in a synergistic herbicidallyeffective amount. In some embodiments, the weight ratio of (a) to (b)can be from 1:3400 to 1200:1 (e.g., from 1:1000 to 1200:1, from 1:1700to 600:1, from 1:280 to 160:1, from 1:200 to 160:1, from 1:7.5 to 160:1,from 1:10 to 16:1, from 1:5 to 5:1, from 2:1 to 16:1, or from 4:1 to8:1).

The pyridine carboxylic acid herbicide can comprise a compound definedby Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is one of groups A1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″), if applicable to the A group, are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₁-C₄haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (II):

wherein

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl. In certain embodiments, R² is Cl, methoxy,vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; A is A15; R⁵ is hydrogenor F; R⁶ is hydrogen or F; and R^(6″) is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (III):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, X is N, CH or CF. In certain embodiments, X is CF,R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀arylalkyl; R² is Cl, methoxy, vinyl, or 1-propenyl; R³ and R⁴ arehydrogen; R⁶ is hydrogen or F; and R^(6′) is hydrogen, halogen, C₁-C₄alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide caninclude 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinicacid, or an agriculturally acceptable N-oxide, salt, or ester thereof.

In some embodiments, (b) can comprise a triazolopyrimidine sulfonamideherbicide. In certain embodiments, (b) can include florasulam,cloransulam, diclosulam, flumetsulam, metosulam, penoxsulam, pyroxsulam,agriculturally acceptable salts or esters thereof, or combinationsthereof.

In some embodiments, (b) can comprise an imidazolinone herbicide. Incertain embodiments, (b) can include imazamethabenz, imazamox, imazapic,imazapyr, imazaquin, imazethapyr, agriculturally acceptable salts oresters thereof, or combinations thereof.

In some embodiments, (b) can comprise a pyrimidinyl oxybenzoateherbicide. In certain embodiments, (b) can include bispyribac,pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac,agriculturally acceptable salts or esters thereof, or combinationsthereof.

In some embodiments, (b) can comprise a sulfonylaminocarbonyltriazolinone herbicide. In certain embodiments, (b) can includeflucarbazone, propoxycarbazone, thiencarbazone, agriculturallyacceptable salts or esters thereof, or combinations thereof.

In some embodiments, (b) can comprise a sulfonylurea herbicide. Incertain embodiments, (b) can include amidosulfuron, azimsulfuron,bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron,ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron,flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron,iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron,sulfosulfuron, triasulfuron, tribenuron, thifensulfuron,trifloxysulfuron, tritosulfuron, agriculturally acceptable salts oresters thereof, or combinations thereof. The composition can furthercomprise an additional pesticide, a herbicidal safener, anagriculturally acceptable adjuvant or carrier, or a combination thereof.The composition can be provided as a herbicidal concentrate.

The present disclosure also relates to methods of controllingundesirable vegetation which comprise applying to vegetation or an areaadjacent the vegetation or applying to soil or water to prevent theemergence or growth of vegetation a herbicidally effective amount of (a)a pyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof and (b) an acetolactate synthase (ALS)inhibitor or an agriculturally acceptable salt or ester thereof. In someembodiments, (a) and (b) are provided in a synergistically effectiveamount. In some embodiments, (a) and (b) are applied simultaneously. Insome embodiments, (a) and (b) are applied post-emergence of theundesirable vegetation.

In some embodiments, (a) can comprise a pyridine carboxylic acidherbicide described above. In certain embodiments, (a) can comprise4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid oran agriculturally acceptable N-oxide, salt, or ester thereof. In someembodiments, (b) can comprise a triazolopyrimidine sulfonamideherbicide. In certain embodiments, (b) can include florasulam,cloransulam, diclosulam, flumetsulam, metosulam, penoxsulam, pyroxsulam,agriculturally acceptable salts or esters thereof, or combinationsthereof. In some cases, (a) can be applied in an amount of from 0.1grams acid equivalent per hectare (g ae/ha) to 300 g ae/ha (e.g., from0.5 g ae/ha to 300 g ae/ha, from 5 g ae/ha to 40 g ae/ha, or from 5 gae/ha to 15 g ae/ha) and/or (b) can be applied in an amount of from 0.25grams active ingredient per hectare (g ai/ha) to 1000 g ai/ha (e.g.,from 0.25 g ai/ha to 7.5 g ai/ha). In some cases, (a) and (b) can beapplied in a weight ratio of from 1:2000 to 1200:1 (e.g., from 1:1000 to1200:1, from 1:200 to 160:1, from 1:50 to 120:1, from 1:7.5 to 160:1,from 1:10 to 16:1, from 1:3.8 to 16:1, from 1:5 to 6:1, from 2:1 to16:1, or from 4:1 to 8:1).

In some embodiments, (a) can comprise a pyridine carboxylic acidherbicide described above. In certain embodiments, (a) can comprise4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid oran agriculturally acceptable N-oxide, salt, or ester thereof. In someembodiments, (b) can comprise an imidazolinone herbicide. In certainembodiments, (b) can include imazamethabenz, imazamox, imazapic,imazapyr, imazaquin, or imazethapyr, or agriculturally acceptable saltsor esters thereof. In some cases, (a) can be applied in an amount offrom 0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha to 300 g ae/ha,from 5 g ae/ha to 40 g ae/ha, or from 5 g ae/ha to 15 g ae/ha) and/or(b) can be applied in an amount of from 5 g ai/ha to 1700 g ai/ha (e.g.,from 10 g ai/ha to 1000 g ai/ha). In some cases, (a) and (b) can beapplied in a weight ratio of from 1:3400 to 60:1 (e.g., from 1:1400 to60:1, from 1:440 to 30:1, from 1:280 to 17:1, or from 1:10 to 5:1).

In some embodiments, (a) can comprise a pyridine carboxylic acidherbicide described above. In certain embodiments, (a) can comprise4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid oran agriculturally acceptable N-oxide, salt, or ester thereof. In someembodiments, (b) can comprise a pyrimidinyl oxybenzoate herbicide. Incertain embodiments, (b) can include bispyribac, pyribenzoxim,pyriftalid, pyriminobac, pyrimisulfan, or pyrithiobac, or agriculturallyacceptable salts or esters thereof. In some cases, (a) can be applied inan amount of from 0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha to300 g ae/ha, from 5 g ae/ha to 40 g ae/ha, or from 5 g ae/ha to 15 gae/ha) and/or (b) can be applied in an amount of from 5 g ai/ha to 300 gai/ha (e.g., from 10 g ai/ha to 200 g ai/ha). In some cases, (a) and (b)can be applied in a weight ratio of from 1:600 to 60:1 (e.g., from 1:140to 40:1, from 1:120 to 20:1, from 1:15 to 4.3:1, or from 1:10 to 5:1).

In some embodiments, (a) can comprise a pyridine carboxylic acidherbicide described above. In certain embodiments, (a) can comprise4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid oran agriculturally acceptable N-oxide, salt, or ester thereof. In someembodiments, (b) can comprise a sulfonylaminocarbonyl triazolinoneherbicide. In certain embodiments, (b) can include flucarbazone,propoxycarbazone, or thiencarbazone, or agriculturally acceptable saltsor esters thereof. In some cases, (a) can be applied in an amount offrom 0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha to 300 g ae/ha,from 5 g ae/ha to 40 g ae/ha, or from 5 g ae/ha to 15 g ae/ha) and/or(b) can be applied in an amount of from 2.5 g ai/ha to 300 g ai/ha(e.g., from 2.5 g ai/ha to 100 g ai/ha). In some cases, (a) and (b) canbe applied in a weight ratio of from 1:600 to 120:1 (e.g., from 1:140 to80:1, from 1:60 to 80:1, from 1:7.5 to 10:1, or from 1:5 to 1:1).

In some embodiments, (b) can comprise a sulfonylurea herbicide. Incertain embodiments, (b) can include amidosulfuron, azimsulfuron,bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron,ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron,flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron,iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron,sulfosulfuron, triasulfuron, tribenuron, thifensulfuron,trifloxysulfuron, tritosulfuron, or agriculturally acceptable salts oresters thereof. In some cases, (a) can be applied in an amount of from0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha to 300 g ae/ha, from5 g ae/ha to 40 g ae/ha, or from 5 g ae/ha to 15 g ae/ha) and/or (b) canbe applied in an amount of from 0.75 g ai/ha to 200 g ai/ha (e.g., from0.75 g ai/ha to 140 g ai/ha). In some cases, (a) and (b) can be appliedin a weight ratio of from 1:400 to 400:1 (e.g., from 1:175 to 70:1, from1:120 to 60:1, from 1:10 to 5:1, or from 1:8.75 to 2:1).

The description below sets forth details of one or more embodiments ofthe present disclosure. Other features, objects, and advantages will beapparent from the description and from the claims.

DETAILED DESCRIPTION

The present disclosure relates to herbicidal compositions comprising aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof and (b) an acetolactate synthase (ALS) inhibitor or anagriculturally acceptable salt or ester thereof. The present disclosurealso relates to methods for controlling undesirable vegetation.

I. Definitions

Terms used herein will have their customary meaning in the art unlessspecified otherwise. The organic moieties mentioned when definingvariable positions within the general formulae described herein (e.g.,the term “halogen”) are collective terms for the individual substituentsencompassed by the organic moiety. The prefix C_(n)-C_(m) preceding agroup or moiety indicates, in each case, the possible number of carbonatoms in the group or moiety that follows.

As used herein, the terms “herbicide” and “herbicidal active ingredient”refer to an active ingredient that kills, controls, or otherwiseadversely modifies the growth of vegetation, particularly undesirablevegetation, such as weeds, when applied in an appropriate amount.

As used herein, a “herbicidally effective amount” refers to an amount ofan active ingredient that causes a “herbicidal effect,” i.e., anadversely modifying effect including, for instance, a deviation fromnatural growth or development, killing, regulation, desiccation, growthinhibition, growth reduction, and retardation.

As used herein, applying a herbicide or herbicidal composition refers todelivering it directly to the targeted vegetation or to the locusthereof or to the area where control of undesired vegetation is desired.Methods of application include, but are not limited to pre-emergentlycontacting soil or water, post-emergently contacting the undesirablevegetation or area adjacent to the undesirable vegetation.

As used herein, the terms “crops” and “vegetation” can include, forinstance, dormant seeds, germinant seeds, emerging seedlings, plantsemerging from vegetative propagules, immature vegetation, andestablished vegetation.

As used herein, immature vegetation refers to small vegetative plantsprior to reproductive stage, and mature vegetation refers to vegetativeplants during and after the reproductive stage.

As used herein, the term “acyl” refers to a group of formula —C(O)R,where R is hydrogen, alkyl (e.g., C₁-C₁₀ alkyl), haloalkyl (C₁-C₈haloalkyl), alkenyl (C₂-C₈ alkenyl), haloalkenyl (e.g., C₂-C₈haloalkenyl), alkynyl (e.g., C₂-C₈ alkynyl), alkoxy (C₁-C₈ alkoxy),haloalkoxy (C₁-C₈ alkoxy), aryl, or heteroaryl, arylalkyl (C₇-C₁₀arylalkyl), as defined below, where “C(O)” or “CO” is short-handnotation for C═O. In some embodiments, the acyl group can be a C₁-C₆acyl group (e.g., a formyl group, a C₁-C₅ alkylcarbonyl group, or aC₁-C₅ haloalkylcarbonyl group). In some embodiments, the acyl group canbe a C₁-C₃ acyl group (e.g., a formyl group, a C₁-C₃ alkylcarbonylgroup, or a C₁-C₃ haloalkylcarbonyl group).

As used herein, the term “alkyl” refers to saturated, straight-chainedor branched saturated hydrocarbon moieties. Unless otherwise specified,C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl groups areintended. Examples of alkyl groups include methyl, ethyl, propyl,1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl-propyl,1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl,3-methyl-butyl, 2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl,1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl-pentyl,2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl,1,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl,2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl,1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1-ethyl-1-methyl-propyl,and 1-ethyl-2-methyl-propyl. Alkyl substituents may be unsubstituted orsubstituted with one or more chemical moieties. Examples of suitablesubstituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl,hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl,aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided thatthe substituents are sterically compatible and the rules of chemicalbonding and strain energy are satisfied. Preferred substituents includecyano and C₁-C₆ alkoxy.

As used herein, the term “haloalkyl” refers to straight-chained orbranched alkyl groups, wherein these groups the hydrogen atoms maypartially or entirely be substituted with halogen atoms. Unlessotherwise specified, C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄)alkyl groups are intended. Examples include chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, and1,1,1-trifluoroprop-2-yl. Haloalkyl substituents may be unsubstituted orsubstituted with one or more chemical moieties. Examples of suitablesubstituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl,hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl,aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided thatthe substituents are sterically compatible and the rules of chemicalbonding and strain energy are satisfied. Preferred substituents includecyano and C₁-C₆ alkoxy.

As used herein, the term “alkenyl” refers to unsaturated,straight-chained, or branched hydrocarbon moieties containing a doublebond. Unless otherwise specified, C₂-C₂₀ (e.g., C₂-C₁₂, C₂-C₁₀, C₂-C₈,C₂-C₆, C₂-C₄) alkenyl groups are intended. Alkenyl groups may containmore than one unsaturated bond. Examples include ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl. The term“vinyl” refers to a group having the structure —CH═CH₂; 1-propenylrefers to a group with the structure —CH═CH—CH₃; and 2-propenyl refersto a group with the structure —CH₂—CH═CH₂. Alkenyl substituents may beunsubstituted or substituted with one or more chemical moieties.Examples of suitable substituents include, for example, hydroxy, nitro,cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl,haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆dihaloalkylaminocarbonyl, provided that the substituents are stericallycompatible and the rules of chemical bonding and strain energy aresatisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

The term “haloalkenyl,” as used herein, refers to an alkenyl group, asdefined above, which is substituted by one or more halogen atoms.

As used herein, the term “alkynyl” represents straight-chained orbranched hydrocarbon moieties containing a triple bond. Unless otherwisespecified, C₂-C₂₀ (e.g., C₂-C₁₂, C₂-C₁₀, C₂-C₈, C₂-C₆, C₂-C₄) alkynylgroups are intended. Alkynyl groups may contain more than oneunsaturated bond. Examples include C₂-C₆-alkynyl, such as ethynyl,1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,3-methyl-I -butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-I-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl,4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.Alkynyl substituents may be unsubstituted or substituted with one ormore chemical moieties. Examples of suitable substituents include, forexample, hydroxy, nitro, cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl,C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl,haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆dihaloalkylaminocarbonyl, provided that the substituents are stericallycompatible and the rules of chemical bonding and strain energy aresatisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

As used herein, the term “alkoxy” refers to a group of the formula R—O—,where R is unsubstituted or substituted alkyl as defined above. Unlessotherwise specified, alkoxy groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂,C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended. Examples includemethoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methyl-propoxy,2-methyl-propoxy, 1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy,2-methyl-butoxy, 3-methyl-butoxy, 2,2-di-methyl-propoxy,1-ethyl-propoxy, hexoxy, 1,1-dimethyl-propoxy, 1,2-dimethyl-propoxy,1-methyl-pentoxy, 2-methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-penoxy,1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy,2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy,1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy,1,2,2-trimethyl-propoxy, 1-ethyl-1-methyl-propoxy, and1-ethyl-2-methyl-propoxy.

As used herein, the term “haloalkoxy” refers to a group of the formulaR—O—, where R is unsubstituted or substituted haloalkyl as definedabove. Unless otherwise specified, haloalkoxy groups wherein R is aC₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) haloalkyl group areintended. Examples include chloromethoxy, bromomethoxy, dichloromethoxy,trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.

As used herein, the term “alkylthio” refers to a group of the formulaR—S—, where R is unsubstituted or substituted alkyl as defined above.Unless otherwise specified, alkylthio groups wherein R is a C₁-C₂₀(e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended.Examples include methylthio, ethylthio, propylthio, 1-methylethylthio,butylthio, 1-methyl-propylthio, 2-methylpropylthio,1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio,3-methylbutylthio, 2,2-di-methylpropylthio, 1-ethylpropylthio,hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,1-methylpentylthio, 2-methylpentylthio, 3-methyl-pentylthio,4-methyl-pentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio,1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

As used herein, the term “haloalkylthio” refers to an alkylthio group asdefined above wherein the carbon atoms are partially or entirelysubstituted with halogen atoms. Unless otherwise specified,haloalkylthio groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈,C₁-C₆, C₁-C₄) alkyl group are intended. Examples includechloromethylthio, bromomethylthio, dichloromethylthio,trichloromethylthio, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorofluoromethylthio, dichlorofluoro-methylthio,chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio,1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,2,2,2-trichloroethylthio, pentafluoroethylthio, and1,1,1-trifluoroprop-2-ylthio.

As used herein, the term “aryl,” as well as derivative terms such asaryloxy, refers to groups that include a monovalent aromatic carbocyclicgroup of from 6 to 14 carbon atoms. Aryl groups can include a singlering or multiple condensed rings. In some embodiments, aryl groupsinclude C₆-C₁₀ aryl groups. Examples of aryl groups include, but are notlimited to, phenyl, biphenyl, naphthyl, tetrahydronaphthyl,phenylcyclopropyl, and indanyl. In some embodiments, the aryl group canbe a phenyl, indanyl or naphthyl group. The term “heteroaryl”, as wellas derivative terms such as “heteroaryloxy”, refers to a 5- or6-membered aromatic ring containing one or more heteroatoms, viz., N, Oor S; these heteroaromatic rings may be fused to other aromatic systems.The aryl or heteroaryl substituents may be unsubstituted or substitutedwith one or more chemical moieties. Examples of suitable substituentsinclude, for example, hydroxy, halogen, nitro, cyano, formyl, C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl,C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl,C₁-C₆ alkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ carbamoyl,hydroxycarbonyl, C₁-C₆ alkylcarbonyl, aminocarbonyl, C₁-C₆alkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, provided that thesubstituents are sterically compatible and the rules of chemical bondingand strain energy are satisfied. Preferred substituents include halogen,C₁-C₂ alkyl and C₁-C₂ haloalkyl.

As used herein, the term “alkylcarbonyl” refers to an unsubstituted orsubstituted alkyl group bonded to a carbonyl group. C₁-C₃ alkylcarbonyland C₁-C₃ haloalkylcarbonyl refer to groups wherein a C₁-C₃unsubstituted or substituted alkyl or haloalkyl group is bonded to acarbonyl group (the group contains a total of 2 to 4 carbon atoms).

As used herein, the term “alkoxycarbonyl” refers to a group of theformula

wherein R is unsubstituted or substituted alkyl.

As used herein, the term “arylalkyl” refers to an alkyl groupsubstituted with an unsubstituted or substituted aryl group. C₇-C₁₀arylalkyl refers to a group wherein the total number of carbon atoms inthe group is 7 to 10, not including the carbon atoms present in anysubstituents of the aryl group.

As used herein, the term “alkylamino” refers to an amino groupsubstituted with one or two unsubstituted or substituted alkyl groups,which may be the same or different.

As used herein, the term “haloalkylamino” refers to an alkylamino groupwherein the alkyl carbon atoms are partially or entirely substitutedwith halogen atoms.

As used herein, C₁-C₆ alkylaminocarbonyl refers to a group of theformula RNHC(O)— wherein R is C₁-C₆ unsubstituted or substituted alkyl,and C₁-C₆ dialkylaminocarbonyl refers to a group of the formula R₂NC(O)—wherein each R is independently C₁-C₆ unsubstituted or substitutedalkyl.

As used herein, the term “alkylcarbamyl” refers to a carbamyl groupsubstituted on the nitrogen with an unsubstituted or substituted alkylgroup.

As used herein, the term “alkylsulfonyl” refers to a group of theformula

where R is unsubstituted or substituted alkyl.

As used herein, the term “carbamyl” (also referred to as carbamoyl andaminocarbonyl) refers to a group of the formula

As used herein, the term “dialkylphosphonyl” refers to a group of theformula

where R is independently unsubstituted or substituted alkyl in eachoccurrence.

As used herein, C₁-C₆ trialkylsilyl refers to a group of the formula—SiR₃ wherein each R is independently a C₁-C₆ unsubstituted orsubstituted alkyl group (the group contains a total of 3 to 18 carbonatoms).

As used herein, Me refers to a methyl group; OMe refers to a methoxygroup; and i-Pr refers to an isopropyl group.

As used herein, the term “halogen” including derivative terms such as“halo” refers to fluorine, chlorine, bromine and iodine.

As used herein, agriculturally acceptable salts and esters refer tosalts and esters that exhibit herbicidal activity, or that are or can beconverted in plants, water, or soil to the referenced herbicide.Exemplary agriculturally acceptable esters are those that are or can behydrolyzed, oxidized, metabolized, or otherwise converted, e.g., inplants, water, or soil, to the corresponding carboxylic acid which,depending on the pH, may be in the dissociated or undissociated form.

Compounds described herein can include N-oxides. Pyridine N-oxides canbe obtained by oxidation of the corresponding pyridines. Suitableoxidation methods are described, for example, in Houben-Weyl, Methodender organischen Chemie [Methods in organic chemistry], expanded andsubsequent volumes to the 4th edition, volume E 7b, p. 565 f.

Pyridine Carboxylic Acid Herbicides

Compositions and methods of the present disclosure can include apyridine carboxylic acid herbicide defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₂-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is one of groups A1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″), if applicable to the A group, are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₁-C₄haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl. In some embodiments, R^(1′) is hydrogen orC₁-C₈ alkyl. In some embodiments, R^(1′) is hydrogen.

In some embodiments, R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄alkynyl, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₁-C₄-alkoxy, or C₁-C₄haloalkoxy. In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄haloalkenyl, or C₁-C₄-alkoxy. In some embodiments, R² is halogen. Insome embodiments, R² is C₂-C₄-alkenyl or C₂-C₄ haloalkenyl. In someembodiments, R² is C₁-C₄ alkoxy. In some embodiments, R² is Cl, OMe,vinyl, or 1-propenyl. In some embodiments, R² is Cl. In someembodiments, R² is OMe. In some embodiments, R² is vinyl or 1-propenyl.

In some embodiments, R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆ alkylcarbamyl, or R³ and R⁴ taken togetherrepresent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independentlyhydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy, orC₁-C₆ alkylamino. In some embodiments, R³ and R⁴ are independentlyhydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) andR^(4′) are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy or C₁-C₆alkylamino. In some embodiments, R³ and R⁴ are independently hydrogen,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl,C₁-C₃ alkylcarbonyl, or C₁-C₃ haloalkylcarbonyl. In some embodiments, atleast one of R³ and R⁴ are hydrogen. In some embodiments, R³ and R⁴ areboth hydrogen.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. Insome embodiments, X is CH. In some embodiments, X is CF. In otherembodiments, X is C—CH₃.

In some embodiments, A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11,A12, A13, A14, A15, A16, A17, A18, A19, or A20. In other embodiments, Ais one of A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32,A33, A34, A35, and A36.

In some embodiments, A is one of groups A1, A2, A3, A7, A8, A9, A10,A13, A14, and A15. In some embodiments, A is one of groups A1, A2, A3,A13, A14, and A15. In some embodiments, A is one of groups A13, A14, andA15. In some embodiments, A is A15.

In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, or amino. In some embodiments, R⁵ is hydrogen, halogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, or amino.In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl or C₁-C₄alkoxy. In some embodiments, R⁵ is hydrogen or F. In some embodiments,R⁵ is hydrogen. In other embodiments, R⁵ is F.

In some embodiments, R⁶ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, or C₁-C₃ haloalkoxy. In some embodiments, R⁶ ishydrogen or fluorine. In some embodiments, R⁶ is hydrogen. In someembodiments, R⁶ is fluorine.

In some embodiments, R^(6′) is hydrogen or halogen. In some embodiments,R^(6′) is hydrogen, F, or Cl. In some embodiments, R^(6′) is hydrogen orF. In some embodiments, R^(6′) is hydrogen.

In some embodiments, R^(6″) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂. In some embodiments,R^(6″) is hydrogen. In some embodiments, R^(6″) is halogen. In someembodiments, R^(6″) is C₁-C₄ alkyl. In some embodiments, R^(6″) is C₁-C₄haloalkyl. In some embodiments, R^(6″) is cyclopropyl. In someembodiments, R^(6″) is C₂-C₄ alkynyl. In some embodiments, R^(6″) is CN.In some embodiments, R^(6″) is NO₂.

In some embodiments:

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl;

R² is chlorine;

R³ and R⁴ are hydrogen;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, OH, amino, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃alkylamino, or cyclopropyl;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, OH, NH₂, CN,C₁-C₃ alkyl, C₁-C₃ alkoxy, cyclopropyl, or vinyl;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃alkoxy, C₁-C₃ alkylthio, cyclopropyl, C₁-C₃ alkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₃ alkyl, phenyl, or C₁-C₃ alkylcarbonyl.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄-alkoxy; R³ and R⁴ are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is halogen; R³ and R⁴ are both hydrogen; and Xis N, CH, or CF.

In some embodiments, R² is C₂-C₄-alkenyl or C₂-C₄ haloalkenyl; R³ and R⁴are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is C₁-C₄-alkoxy; R³ and R⁴ are both hydrogen;and X is N, CH, or CF.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄-alkoxy;

R³ and R⁴ are both hydrogen; X is N, CH, or CF; R⁵ is hydrogen or F; R⁶is hydrogen or F; R^(6′) is hydrogen; R^(6″), if applicable to therelevant A group, is hydrogen or halogen; and R⁷ and R^(7′), ifapplicable to the relevant A group, are independently hydrogen orhalogen.

In some embodiments, R² is halogen, C₁-C₄-alkoxy, or C₂-C₄-alkenyl; R³and R⁴ are hydrogen; Xis N, CH, or CF; and A is one of groups A1 to A20.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; X is N, CH,or CF; A is one of groups A1 to A20; R⁵ is hydrogen or F; R⁶ and R^(6′)are independently hydrogen or F; and R⁷ and R^(7′), if applicable to therelevant A group, are independently hydrogen, halogen, C₁-C₄ alkyl, orC₁-C₄ haloalkyl.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; and X is N, CH, or CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is N,CH, or CF.

In some embodiments, R² is vinyl or 1-propenyl; R³ and R⁴ are hydrogen;and X is N, CH, or CF.

In some embodiments, R² is methoxy; R³ and R⁴ are hydrogen; and X is N,CH, or CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is N.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X isCH.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X isCF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; X is CF; Ais one of A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15; R⁵ is F; and R⁶is H.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is one of A21-A36.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is CF; and A is one of

wherein R⁵ is hydrogen or F.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is

where R⁵ is hydrogen or F.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is N, CH, or CF; and A is

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³and R⁴ are hydrogen; X is CF; and A is

In some embodiments, the pyridine carboxylic acid herbicide can comprisea compound defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹² ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof,

with the proviso that the pyridine carboxylic acid herbicide is not acompound defined by Formula (I)

wherein

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl;

R² is chlorine;

R³ and R⁴ are hydrogen;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, OH, amino, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃alkylamino, or cyclopropyl;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, OH, NH₂, CN,C₁-C₃ alkyl, C₁-C₃ alkoxy, cyclopropyl, or vinyl;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃alkoxy, C₁-C₃ alkylthio, cyclopropyl, C₁-C₃ alkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₃ alkyl, phenyl, or C₁-C₃ alkylcarbonyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is CY, wherein Y is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1′)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Ais A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is C₅-C₈ alkyl, orC₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and are independently hydrogen,C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is F, Br, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(″) and R^(′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33,A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halocyclopropyl, C₂-C₄ alkenyl,C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio,C₁-C₃ haloalkylthio, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently C₁-C₄ alkyl, C₁-C₄ haloalkyl,halocyclopropyl, C₃-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₄ alkylamino orC₂-C₄ haloalkylamino, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, or A18;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently C₁-C₄ alkyl, C₁-C₄ haloalkyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃haloalkoxy, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄haloalkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A3, A6, A11, A12, A15, A18, A19, or A20;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is C₃-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl,C₃-C₆ alkynyl, formyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ trialkylsilyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, Xis CF. In some of these embodiments, A is A15. In some of theseembodiments, R⁵ is F.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (II):

wherein

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₂-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15,A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29,A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments:

R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, or C₁-C₄ haloalkylthio;

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino;

A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15, A21, A22,A23, A24, A27, A28, A29, A30, A31, or A32;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl,C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄haloalkylamino;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl,amino or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈alkyl, or C₇-C₁₀ arylalkyl.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄-alkoxy. In certain embodiments, R² is Cl, methoxy, vinyl, or1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15.In certain embodiments, A is A1, A2, A3, A13, A14, or A15. In certainembodiments, A is A15.

In some embodiments, R⁵ is hydrogen or F. In certain embodiments, R⁵ isF. In certain embodiments, R⁵ is H.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ isF. In certain embodiments, R⁶ is H. In some embodiments, R^(6″) ishydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄alkynyl, CN, or NO₂. In certain embodiments, R⁶, R^(6′), and R^(6″) areall hydrogen.

In certain embodiments, R² is Cl, methoxy, vinyl, or 1-propenyl; R³ andR⁴ are hydrogen; A is A15; R⁵ is hydrogen or F; R⁶ is hydrogen or F; andR^(6″) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise a compound defined by Formula (III):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen, C₁-Csalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) are independentlyhydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or6-membered saturated ring, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5-or 6-membered saturated ring;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments:

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, or C₁-C₄ haloalkylthio;

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl,amino or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. Insome embodiments, X is CH. In some embodiments, X is CF. In otherembodiments, X is C—CH₃.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, orC₁-C₄ alkoxy. In certain embodiments, R² is Cl, methoxy, vinyl, or1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ isF. In certain embodiments, R⁶ is H. In some embodiments, R^(6′) ishydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄alkynyl, CN, or NO₂. In certain embodiments, R⁶ and R^(6′) are bothhydrogen.

In certain embodiments, R⁷ and R^(7′) are both hydrogen.

In certain embodiments, R⁶, R^(6′), R⁷, and R^(7′) are all hydrogen.

In certain embodiments, X is CF, R¹ is OR^(1′), wherein R^(1′) ishydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl; R² is Cl, methoxy, vinyl, or1-propenyl; R³ and R⁴ are hydrogen; R⁶ is hydrogen or F; and R^(6′) ishydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise one of Compounds 1-24, the structures of which are shown in thetable below.

Compound No. Structure 1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

In certain embodiments, the pyridine carboxylic acid herbicide cancomprise 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinicacid or an agriculturally acceptable N-oxide, salt, or ester thereof.

In some embodiments, the pyridine carboxylic acid herbicide can beprovided as an agriculturally acceptable salt. Exemplary agriculturallyacceptable salts of the pyridine carboxylic acid herbicides of Formula(I) include, but are not limited to, sodium salts, potassium salts,ammonium salts or substituted ammonium salts, in particular mono-, di-and tri-C₁-C₈-alkylammonium salts such as methyl ammonium,dimethylammonium and isopropylammonium, mono-, di- andtri-hydroxy-C₂-C₈-alkylammonium salts such as hydroxyethylammonium,di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium,hydroxypropylammonium, di(hydroxypropyl)ammonium andtri(hydroxypropyl)ammonium salts, olamine salts, diglycolamine salts,choline salts, and quaternary ammonium salts such as those representedby the formula R⁹R¹⁰R¹¹R¹²N⁺ and wherein R⁹, R¹⁰, R¹¹ and R¹² (e.g.,R⁹-R¹²) each independently can represent hydrogen, C₁-C₁₀ alkyl, C₂-C₈alkenyl, C₂-C₈ alkynyl, C₁-C₈ alkoxy, C₁-C₈ alkylthio, or aryl groups,provided that R⁹-R¹² are sterically compatible.

In some embodiments, the pyridine carboxylic acid herbicide can beprovided as an agriculturally acceptable ester. Suitable esters include,but are not limited to, C₁-C₈-alkyl esters and C₁-C₄-alkoxy-C₂-C₄-alkylesters, such as methyl esters, ethyl esters, isopropyl, butyl, hexyl,heptyl, isoheptyl, isooctyl, 2-ethylhexyl, butoxyethyl esters,substituted or unsubstituted aryl esters, orthoesters, substituted orunsubstituted alkylaryl esters, and substituted or unsubstitutedarylalkyl esters. In some embodiments, the ester can comprise a C₁-C₈alkyl ester, wherein the C₁-C₈ alkyl group is optionally substitutedwith one or more moieties selected from the group consisting of cyano,C₂-C₈ alkoxy, and C₂-C₈ alkylsulfonyl. For example, the ester cancomprise a methyl, —CH₂CN, —CH₂OCH₃, —CH₂OCH₂CH₂OCH₃, or —CH₂CH₂SO₂CH₃ester.

The ester can also be an acetal (e.g., a cyclic acetal) formed byprotection of the carbonyl group in the pyridine carboxylic acidherbicides described above (e.g., by Formula (I)). For example, thepyridine carboxylic acid herbicides described above can be reacted witha suitable diol (e.g., a diol such as ethane-1,2-diol orbutane-2,3-diol, for example, using standard protecting group chemistry,such as taught in Greene, et al., Protective Groups in OrganicSynthesis, John Wiley and Sons, Fourth Edition, 2007, herebyincorporated by reference) to form a cyclic acetal. In one embodiment,the ester can be a cyclic acetal defined by the structure below, whereR², R³, R⁴, X, and A are as described above.

In some embodiments, the ester can comprise a substituted orunsubstituted benzyl ester. In some embodiments, the ester can comprisea benzyl ester optionally substituted with one or more moieties selectedfrom the group consisting of halogen, C₁-C₂ alkyl, C₁-C₂ haloalkyl, andcombinations thereof. In some embodiments, the ester can comprise amethyl ester.

The pyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof can be applied to vegetation or an areaadjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount sufficient to induce aherbicidal effect. In some embodiments, the pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 0.1 grams of acid equivalent per hectare (gae/ha) or greater (e.g.,0.2 g ae/ha or greater, 0.3 g ae/ha or greater,0.4 g ae/ha or greater, 0.5 g ae/ha or greater, 0.6 g ae/ha or greater,0.7 g ae/ha or greater, 0.8 g ae/ha or greater, 0.9 g ae/ha or greater,1 g ae/ha or greater, 1.1 g ae/ha or greater, 1.2 g ae/ha or greater,1.3 g ae/ha or greater, 1.4 g ae/ha or greater, 1.5 g ae/ha or greater,1.6 g ae/ha or greater, 1.7 g ae/ha or greater, 1.8 g ae/ha or greater,1.9 g ae/ha or greater, 2 g ae/ha or greater, 2.25 g ae/ha or greater,2.5 g ae/ha or greater, 2.75 g ae/ha or greater, 3 g ae/ha or greater, 4g ae/ha or greater, 5 g ae/ha or greater, 6 g ae/ha or greater, 7 gae/ha or greater, 8 g ae/ha or greater, 9 g ae/ha or greater, 10 g ae/haor greater, 11 g ae/ha or greater, 12 g ae/ha or greater, 13 g ae/ha orgreater, 14 g ae/ha or greater, 15 g ae/ha or greater, 16 g ae/ha orgreater, 17 g ae/ha or greater, 18 g ae/ha or greater, 19 g ae/ha orgreater, 20 g ae/ha or greater, 21 g ae/ha or greater, 22 g ae/ha orgreater, 23 g ae/ha or greater, 24 g ae/ha or greater, 25 g ae/ha orgreater, 26 g ae/ha or greater, 27 g ae/ha or greater, 28 g ae/ha orgreater, 29 g ae/ha or greater, 30 g ae/ha or greater, 31 g ae/ha orgreater, 32 g ae/ha or greater, 33 g ae/ha or greater, 34 g ae/ha orgreater, 35 g ae/ha or greater, 36 g ae/ha or greater, 37 g ae/ha orgreater, 38 g ae/ha or greater, 39 g ae/ha or greater, 40 g ae/ha orgreater, 41 g ae/ha or greater, 42 g ae/ha or greater, 43 g ae/ha orgreater, 44 g ae/ha or greater, 45 g ae/ha or greater, 46 g ae/ha orgreater, 47 g ae/ha or greater, 48 g ae/ha or greater, 49 g ae/ha orgreater, 50 g ae/ha or greater, 55 g ae/ha or greater, 60 g ae/ha orgreater, 65 g ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha orgreater, 80 g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha orgreater, 95 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha orgreater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g ae/ha orgreater, 150 g ae/ha or greater, 160 g ae/ha or greater, 170 g ae/ha orgreater, 180 g ae/ha or greater, 190 g ae/ha or greater, 200 g ae/ha orgreater, 210 g ae/ha or greater, 220 g ae/ha or greater, 230 g ae/ha orgreater, 240 g ae/ha or greater, 250 g ae/ha or greater, 260 g ae/ha orgreater, 270 g ae/ha or greater, 280 g ae/ha or greater, or 290 g ae/haor greater).

In some embodiments, the pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of300 g ae/ha or less (e.g., 290 g ae/ha or less, 280 g ae/ha or less, 270g ae/ha or less, 260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/haor less, 230 g ae/ha or less, 220 g ae/ha or less, 210 g ae/ha or less,200 g ae/ha or less, 190 g ae/ha or less, 180 g ae/ha or less, 170 gae/ha or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha orless, 130 g ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100g ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha orless, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or less, 65 gae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less, 50 g ae/ha orless, 49 g ae/ha or less, 48 g ae/ha or less, 47 g ae/ha or less, 46 gae/ha or less, 45 g ae/ha or less, 44 g ae/ha or less, 43 g ae/ha orless, 42 g ae/ha or less, 41 g ae/ha or less, 40 g ae/ha or less, 39 gae/ha or less, 38 g ae/ha or less, 37 g ae/ha or less, 36 g ae/ha orless, 35 g ae/ha or less, 34 g ae/ha or less, 33 g ae/ha or less, 32 gae/ha or less, 31 g ae/ha or less, 30 g ae/ha or less, 29 g ae/ha orless, 28 g ae/ha or less, 27 g ae/ha or less, 26 g ae/ha or less, 25 gae/ha or less, 24 g ae/ha or less, 23 g ae/ha or less, 22 g ae/ha orless, 21 g ae/ha or less, 20 g ae/ha or less, 19 g ae/ha or less, 18 gae/ha or less, 17 g ae/ha or less, 16 g ae/ha or less, 15 g ae/ha orless, 14 g ae/ha or less, 13 g ae/ha or less, 12 g ae/ha or less, 11 gae/ha or less, 10 g ae/ha or less, 9 g ae/ha or less, 8 g ae/ha or less,7 g ae/ha or less, 6 g ae/ha or less, 5 g ae/ha or less, 4 g ae/ha orless, 3 g ae/ha or less, 2.75 g ae/ha or less, 2.5 g ae/ha or less, 2.25g ae/ha or less, 2 g ae/ha or less, 1.9 g ae/ha or less, 1.8 g ae/ha orless, 1.7 g ae/ha or less, 1.6 g ae/ha or less, 1.5 g ae/ha or less, 1.4g ae/ha or less, 1.3 g ae/ha or less, 1.2 g ae/ha or less, 1.1 g ae/haor less, 1 g ae/ha or less, 0.9 g ae/ha or less, 0.8 g ae/ha or less,0.7 g ae/ha or less, 0.6 g ae/ha or less, 0.5 g ae/ha or less, 0.4 gae/ha or less, 0.3 g ae/ha or less, or 0.2 g ae/ha or less).

The pyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof can be applied to vegetation or an areaadjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount ranging from any of theminimum values described above to any of the maximum values describedabove. In some embodiments, the pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount offrom 0.1-300 g ae/ha (e.g., from 0.5-300 g ae/ha, from 0.1-5 g ae/ha,from 0.5-5 g ae/ha, from 2.5-40 g ae/ha, from 0.1-40 g ae/ha, from0.5-40 g ae/ha, from 0.1-2.5 g ae/ha, from 0.5-2.5 g ae/ha, from 2-150 gae/ha, from 5-75 g ae/ha, from 5-40 g ae/ha, from 30-40 g ae/ha, or from5-15 g ae/ha). In some embodiments, the pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof is applied in an amount from 5-40 g ae/ha. In some embodiments,the pyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof is applied in an amount from 30-40 gae/ha. In some embodiments, the pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof is applied inan amount from 5-15 g ae/ha.

ALS Inhibitors

In addition to the pyridine carboxylic acid herbicide or agriculturallyacceptable N-oxide, salt or ester thereof, the compositions can includean acetolactate synthase (ALS) inhibitor. ALS inhibitors disrupt theproduction of amino acids in the plant, which eventually leads toinhibition of DNA synthesis. Examples of ALS inhibitors includesulfonylureas, imidazolinones, triazolopyrimidine sulfonamides,pyrimidinyl oxybenzoates and sulfonylaminocarbonyl triazolinones. Insome embodiments, the ALS inhibitor can comprise a triazolopyrimidinesulfonamide herbicide. In some embodiments, the ALS inhibitor cancomprise an imidazolinone herbicide. In some embodiments, the ALSinhibitor can comprise a pyrimidinyl oxybenzoate herbicide. In someembodiments, the ALS inhibitor can comprise a sulfonylaminocarbonyltriazolinone herbicide. In some embodiments, the ALS inhibitor cancomprise a sulfonylurea herbicide.

In some embodiments, the composition can include an ALS inhibitorselected from the group consisting of imidazolinones, triazolopyrimidinesulfonamides, pyrimidinyl oxybenzoates, sulfonylaminocarbonyltriazolinones, sulfonylureas, and combinations thereof. In some cases,the composition can include penoxsulam, amidosulfuron, azimsulfuron,bispyribac, bensulfuron, chlorimuron, clorsulfuron, cinosulfuron,cloransulam, cyclosulfamuron, diclosulam, ethametsulfuron,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone,flucetosulfuron, flumetsulam, flupyrsulfuron, foramsulfuron,halosulfuron, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron,metazosulfuron, metosulam, metsulfuron, nicosulfuron, orthosulfamuron,oxasulfuron, primisulfuron, propoxycarbazone, propyrisulfuron,prosulfuron, pyrazosulfuron, pyribenzoxim, pyriftalid, pyriminobac,pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam, rimsulfuron,sulfometuron, sulfosulfuron, thiencarbazone, thifensulfuron,thiencarbazone, triasulfuron, tribenuron, thifensulfuron,trifloxysulfuron, tritosulfuron, agriculturally acceptable salts andesters thereof, and combinations thereof.

The ALS inhibitor or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the ALS inhibitor or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 0.25 grams active ingredient per hectare (g ai/ha) or more(e.g., 0.3 g ai/ha or more, 0.4 g ai/ha or more, 0.5 g ai/ha or more,0.6 g ai/ha or more, 0.7 g ai/ha or more, 0.8 g ai/ha or more, 0.9 gai/ha or more, 1 g ai/ha or more, 1.5 g ai/ha or more, 2 g ai/ha ormore, 2.5 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 gai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha ormore, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 gai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha ormore, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 gai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha ormore, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 gai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha ormore, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/haor more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more,200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 230 gai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha ormore, 270 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/haor more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more,370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 gai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha ormore, 480 g ai/ha or more, 500 g ai/ha or more, 520 g ai/ha or more, 540g ai/ha or more, 560 g ai/ha or more, 580 g ai/ha or more, 600 g ai/haor more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more,700 g ai/ha or more, 725 g ai/ha or more, 750 g ai/ha or more, 775 gai/ha or more, 800 g ai/ha or more, 825 g ai/ha or more, 850 g ai/ha ormore, 875 g ai/ha or more, 900 g ai/ha or more, 925 g ai/ha or more, 950g ai/ha or more, 975 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/haor more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha ormore, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more,1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 gai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, 1660 g ai/haor more, 1670 g ai/ha or more, 1680 g ai/ha or more, or 1690 g ai/ha ormore).

In some embodiments, the ALS inhibitor or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 1700 g ai/ha or less (e.g., 1690 gai/ha or less, 1680 g ai/ha or less, 1670 g ai/ha or less, 1660 g ai/haor less, 1650 g ai/ha or less, 1600 g ai/ha or less, 1550 g ai/ha orless, 1500 g ai/ha or less, 1450 g ai/ha or less, 1400 g ai/ha or less,1350 g ai/ha or less, 1300 g ai/ha or less, 1250 g ai/ha or less, 1200 gai/ha or less, 1150 g ai/ha or less, 1100 g ai/ha or less, 1050 g ai/haor less, 1000 g ai/ha or less, 975 g ai/ha or less, 950 g ai/ha or less,925 g ai/ha or less, 900 g ai/ha or less, 875 g ai/ha or less, 850 gai/ha or less, 825 g ai/ha or less, 800 g ai/ha or less, 775 g ai/ha orless, 750 g ai/ha or less, 725 g ai/ha or less, 700 g ai/ha or less, 675g ai/ha or less, 650 g ai/ha or less, 625 g ai/ha or less, 600 g ai/haor less, 580 g ai/ha or less, 560 g ai/ha or less, 540 g ai/ha or less,520 g ai/ha or less, 500 g ai/ha or less, 480 g ai/ha or less, 460 gai/ha or less, 440 g ai/ha or less, 420 g ai/ha or less, 400 g ai/ha orless, 390 g ai/ha or less, 380 g ai/ha or less, 370 g ai/ha or less, 360g ai/ha or less, 350 g ai/ha or less, 340 g ai/ha or less, 330 g ai/haor less, 320 g ai/ha or less, 310 g ai/ha or less, 300 g ai/ha or less,290 g ai/ha or less, 280 g ai/ha or less, 270 g ai/ha or less, 260 gai/ha or less, 250 g ai/ha or less, 240 g ai/ha or less, 230 g ai/ha orless, 220 g ai/ha or less, 210 g ai/ha or less, 200 g ai/ha or less, 190g ai/ha or less, 180 g ai/ha or less, 170 g ai/ha or less, 160 g ai/haor less, 150 g ai/ha or less, 140 g ai/ha or less, 130 g ai/ha or less,120 g ai/ha or less, 110 g ai/ha or less, 100 g ai/ha or less, 95 gai/ha or less, 90 g ai/ha or less, 85 g ai/ha or less, 80 g ai/ha orless, 75 g ai/ha or less, 70 g ai/ha or less, 65 g ai/ha or less, 60 gai/ha or less, 55 g ai/ha or less, 50 g ai/ha or less, 45 g ai/ha orless, 40 g ai/ha or less, 35 g ai/ha or less, 30 g ai/ha or less, 25 gai/ha or less, 20 g ai/ha or less, 15 g ai/ha or less, 10 g ai/ha orless, 9 g ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/haor less, 5 g ai/ha or less, 4.5 g ai/ha or less, 4 g ai/ha or less, 3.5g ai/ha or less, 3 g ai/ha or less, 2.5 g ai/ha or less, 2 g ai/ha orless, 1.5 g ai/ha or less, 1 g ai/ha or less, 0.9 g ai/ha or less, 0.8 gai/ha or less, 0.7 g ai/ha or less, 0.6 g ai/ha or less, 0.5 g ai/ha orless, 0.4 g ai/ha or less, or 0.3 g ai/ha or less).

The ALS inhibitor or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the ALS inhibitor or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 0.25-1700 g ai/ha (e.g., 0.25-1250 g ai/ha, 1250-1700 g ai/ha,0.25-1200 g ai/ha, 0.25-1150 g ai/ha, 0.25-1100 g ai/ha, 0.25-1060 gai/ha, 0.25-1000 g ai/ha, 0.25-900 g ai/ha, 0.25-800 g ai/ha, 0.25-750 gai/ha, 750-1000 g ai/ha, 0.25-700 g ai/ha, 0.25-650 g ai/ha, 0.25-600 gai/ha, 0.25-560 g ai/ha, 0.25-500 g ai/ha, 0.25-460 g ai/ha, 0.25-400 gai/ha, 0.25-460 g ai/ha, 0.25-400 g ai/ha, 0.25-360 g ai/ha, 0.25-300 gai/ha, 0.25-280 g ai/ha, 5-260 g ai/ha, 0.25-240 g ai/ha, 0.25-220 gai/ha, 0.25-200 g ai/ha, 0.25-180 g ai/ha, 0.25-160 g ai/ha, 0.25-140 gai/ha, 0.25-120 g ai/ha, 0.25-100 g ai/ha, 0.25-90 g ai/ha, 0.25-80 gai/ha, 0.25-70 g ai/ha, 0.25-60 g ai/ha, 0.25-50 g ai/ha, 0.25-40 gai/ha, 0.25-30 g ai/ha, 0.25-20 g ai/ha, 0.25-10 g ai/ha, 10-560 gai/ha, 20-500 g ai/ha, 30-460 g ai/ha, 40-400 g ai/ha, 50-360 g ai/ha,60-300 g ai/ha, 70-280 g ai/ha, 70-100 g ai/ha, 70-140 g ai/ha, 100-140g ai/ha, 100-280 g ai/ha, or 140-280 g ai/ha).

In certain embodiments, the herbicidal composition comprises aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof, and (b) florasulam, cloransulam, diclosulam, flumetsulam,metosulam, penoxsulam, pyroxsulam, agriculturally acceptable salts oresters thereof, or combinations thereof.

Florasulam

Compositions and methods of the present disclosure can includeflorasulam or an agriculturally acceptable salt thereof. Florasulam,shown below, is a triazolopyrimidine sulfonamide that providesbroad-spectrum control of many broad-leaved weeds in cereals and maize.Florasulam, as well as methods of preparing florasulam, are known in theart. Its herbicidal activity is described, for example, in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, florasulam can be provided as an agriculturallyacceptable salt of florasulam.

The florasulam or agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, theflorasulam or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of0.25 g ai/ha or more (e.g., 0.3 g ai/ha or more, 0.4 g ai/ha or more,0.5 g ai/ha or more, 0.6 g ai/ha or more, 0.7 g ai/ha or more, 0.8 gai/ha or more, 0.9 g ai/ha or more, 1 g ai/ha or more, 1.1 g ai/ha ormore, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/haor more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more,3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 gai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g ai/ha ormore, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more, 6.25g ai/ha or more, 6.5 g ai/ha or more, 6.75 g ai/ha or more, 7 g ai/ha ormore, or 7.25 g ai/ha or more).

In some embodiments, the florasulam or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 7.5 g ai/ha or less (e.g., 7.25 g ai/ha orless, 7 g ai/ha or less, 6.75 g ai/ha or less, 6.5 g ai/ha or less, 6.25g ai/ha or less, 6 g ai/ha or less, 5.75 g ai/ha or less, 5.5 g ai/ha orless, 5.25 g ai/ha or less, 5 g ai/ha or less, 4.75 g ai/ha or less, 4.5g ai/ha or less, 4.25 g ai/ha or less, 4 g ai/ha or less, 3.75 g ai/haor less, 3.5 g ai/ha or less, 3.25 g ai/ha or less, 3 g ai/ha or less,2.75 g ai/ha or less, 2.5 g ai/ha or less, 2.25 g ai/ha or less, 2 gai/ha or less, 1.75 g ai/ha or less, 1.5 g ai/ha or less, 1.25 g ai/haor less, 1 g ai/ha or less, 0.9 g ai/ha or less, 0.8 g ai/ha or less,0.7 g ai/ha or less, 0.6 g ai/ha or less, 0.5 g ai/ha or less, 0.4 gai/ha or less, or 0.3 g ai/ha or less).

The florasulam or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the florasulamor agriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 0.25-7.5 g ai/ha(e.g., 0.25-7 g ai/ha, 0.25-6.5 g ai/ha, 0.25-6 g ai/ha, 0.25-5.5 gai/ha, 0.25-5 g ai/ha, 0.25-4.5 g ai/ha, 0.25-4 g ai/ha, 0.25-3.5 gai/ha, 0.25-3 g ai/ha, 0.25-2.5 g ai/ha, 0.5-2 g ai/ha, 0.75-1.75 gai/ha, or 1-1.5 g ai/ha).

Cloransulam

Compositions and methods of the present disclosure can includecloransulam or an agriculturally acceptable salt thereof. Cloransulam,as well as methods of preparing cloransulam, are known in the art. Insome embodiments, cloransulam can be provided as an agriculturallyacceptable ester of cloransulam. Cloransulam-methyl, shown below, is atriazolopyrimidine sulfonamide that provides broad-spectrum control ofmany broadleaf weeds in soybeans and other broadleaf crops. Itsherbicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009.

The cloransulam or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the cloransulam or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 2.18 g ai/ha or more (e.g., 2.25 g ai/ha or more, 2.5 g ai/haor more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more,3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 gai/ha or less, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha ormore, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 gai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha ormore, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 gai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha ormore, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 gai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha ormore, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 gai/ha or more, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha ormore, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 gai/ha or more, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha ormore, 42 g ai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 gai/ha or more, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha ormore, 49 g ai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 gai/ha or more, 53 g ai/ha or more, 54 g ai/ha or more, 55 g ai/ha ormore, 56 g ai/ha or more, 57 g ai/ha or more, 58 g ai/ha or more, 59 gai/ha or more, or 60 g ai/ha or more).

In some embodiments, the cloransulam or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 61 g ai/ha or less (e.g., 60 g ai/ha or less,59 g ai/ha or less, 58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/haor less, 55 g ai/ha or less, 54 g ai/ha or less, 53 g ai/ha or less, 52g ai/ha or less, 51 g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha orless, 48 g ai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 gai/ha or less, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha orless, 41 g ai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 gai/ha or less, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha orless, 34 g ai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 gai/ha or less, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha orless, 27 g ai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 gai/ha or less, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha orless, 20 g ai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 gai/ha or less, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha orless, 13 g ai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 gai/ha or less, 9 g ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less,6 g ai/ha or less, 5 g ai/ha or less, 4.5 g ai/ha or less, 4.25 g ai/haor less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5 g ai/ha or less,3.25 g ai/ha or less, 3 g ai/ha or less, 2.75 g ai/ha or less, 2.5 gai/ha or less, or 2.25 g ai/ha or less).

The cloransulam or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the cloransulam or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.18-61 g ai/ha (e.g., 2.5-60 g ai/ha, 2.75-55 g ai/ha, 3-50 g ai/ha,3.25-60 g ai/ha, 3.5-50 g ai/ha, 3.75-60 g ai/ha, 3.75-50 g ai/ha, 4-60g ai/ha, 4-50 g ai/ha, 4.25-60 g ai/ha, 4.25-55 g ai/ha, 4.25-50 gai/ha, or 4.25-45 g ai/ha).

Diclosulam

Compositions and methods of the present disclosure can includediclosulam or an agriculturally acceptable salt thereof. Diclosulam,shown below, is a triazolopyrimidine sulfonamide that providesbroad-spectrum control of many broadleaf weeds in soybeans and peanuts.Diclosulam, as well as methods of preparing diclosulam, are known in theart. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, diclosulam can be provided as an agriculturallyacceptable salt of diclosulam.

The diclosulam or agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, thediclosulam or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.18 g ai/ha or more (e.g., 2.25 g ai/ha or more, 2.5 g ai/ha or more,2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 gai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha ormore, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.5g ai/ha or more, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha ormore, 7.5 g ai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 gai/ha or more, 9.5 g ai/ha or more, 10 g ai/ha or more, 10.5 g ai/ha ormore, 11 g ai/ha or more, 11.5 g ai/ha or more, 12 g ai/ha or more, 12.5g ai/ha or more, 13 g ai/ha or more, 13.5 g ai/ha or more, 14 g ai/ha ormore, 14.5 g ai/ha or more, 15 g ai/ha or more, 15.5 g ai/ha or more, 16g ai/ha or more, 16.5 g ai/ha or more, 17 g ai/ha or more, 17.5 g ai/haor more, 18 g ai/ha or more, 18.5 g ai/ha or more, 19 g ai/ha or more,19.5 g ai/ha or more, 20 g ai/ha or more, 20.5 g ai/ha or more, 21 gai/ha or more, 21.5 g ai/ha or more, 22 g ai/ha or more, 22.5 g ai/ha ormore, 23 g ai/ha or more, 23.5 g ai/ha or more, 24 g ai/ha or more, 24.5g ai/ha or more, 25 g ai/ha or more, 25.5 g ai/ha or more, 26 g ai/ha ormore, 26.5 g ai/ha or more, 27 g ai/ha or more, 27.5 g ai/ha or more, 28g ai/ha or more, 28.5 g ai/ha or more, 29 g ai/ha or more, 29.5 g ai/haor more, 30 g ai/ha or more, 30.5 g ai/ha or more, 31g ai/ha or more,31.5 g ai/ha or more, 32 g ai/ha or more, 32.5 g ai/ha or more, 33 gai/ha or more, 33.5 g ai/ha or more, 34 g ai/ha or more, 34.5 g ai/ha ormore, or 34.75 g ai/ha or more).

In some embodiments, the diclosulam or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 35 g ai/ha or less (e.g., 34.5 g ai/ha orless, 34 g ai/ha or less, 33.5 g ai/ha or less, 33 g ai/ha or less, 32.5g ai/ha or less, 32 g ai/ha or less, 31.5 g ai/ha or less, 31 g ai/ha orless, 30.5 g ai/ha or less, 30 g ai/ha or less, 29.5 g ai/ha or less, 29g ai/ha or less, 28.5 g ai/ha or less, 28 g ai/ha or less, 27.5 g ai/haor less, 27 g ai/ha or less, 26.5 g ai/ha or less, 26 g ai/ha or less,25.5 g ai/ha or less, 25 g ai/ha or less, 24.5 g ai/ha or less, 24 gai/ha or less, 23.5 g ai/ha or less, 23 g ai/ha or less, 22.5 g ai/ha orless, 22 g ai/ha or less, 21.5 g ai/ha or less, 21 g ai/ha or less, 20.5g ai/ha or less, 20 g ai/ha or less, 19.5 g ai/ha or less, 19 g ai/ha orless, 18.5 g ai/ha or less, 18 g ai/ha or less, 17.5 g ai/ha or less, 17g ai/ha or less, 16.5 g ai/ha or less, 16 g ai/ha or less, 15.5 g ai/haor less, 15 g ai/ha or less, 14.5 g ai/ha or less, 14 g ai/ha or less,13.5 g ai/ha or less, 13 g ai/ha or less, 12.5 g ai/ha or less, 12 gai/ha or less, 11.5 g ai/ha or less, 11 g ai/ha or less, 10.5 g ai/ha orless, 10 g ai/ha or less, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5 gai/ha or less, 8 g ai/ha or less, 7.5 g ai/ha or less, 7 g ai/ha orless, 6.5 g ai/ha or less, 6 g ai/ha or less, 5.5 g ai/ha or less, 5 gai/ha or less, 4.75 g ai/ha or less, 4.5 g ai/ha or less, 4.25 g ai/haor less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5 g ai/ha or less,2.75 g ai/ha or less, 2.5 g ai/ha or less, or 2.25 g ai/ha or less).

The diclosulam or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the diclosulamor agriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 2.18-35 g ai/ha (e.g.,2.5-34 g ai/ha, 2.75-32 g ai/ha, 3-30 g ai/ha, 3.25-35 g ai/ha, 3.25-32g ai/ha, 3.5-30 g ai/ha, 3.75-34 g ai/ha, 4-35 g ai/ha, 4-30 g ai/ha,4.25-35 g ai/ha, 4.25-34 g ai/ha, 4.25-32 g ai/ha, or 4.25-30 g ai/ha).

Flumetsulam

Compositions and methods of the present disclosure can includeflumetsulam or an agriculturally acceptable salt thereof. Flumetsulam,shown below, is a triazolopyrimidine sulfonamide that provides controlof broadleaf weeds and greens in soybeans, field peas, and maize.Flumetsulam, as well as methods of preparing flumetsulam, are known inthe art. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, flumetsulam can be provided as an agriculturallyacceptable salt of flumetsulam.

The flumetsulam or agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, theflumetsulam or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.18 g ai/ha or more (e.g., 2.25 g ai/ha or more, 2.5 g ai/ha or more,2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 gai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha ormore, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 6 gai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more,10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/haor more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha ormore, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 gai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha ormore, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 gai/ha or more, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha ormore, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 gai/ha or more, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha ormore, 42 g ai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 gai/ha or more, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha ormore, 49 g ai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 gai/ha or more, 53 g ai/ha or more, 54 g ai/ha or more, 55 g ai/ha ormore, 56 g ai/ha or more, 57 g ai/ha or more, 58 g ai/ha or more, 59 gai/ha or more, 60 g ai/ha or more, 61 g ai/ha or more, 62 g ai/ha ormore, 63 g ai/ha or more, 64 g ai/ha or more, 65 g ai/ha or more, 66 gai/ha or more, 67 g ai/ha or more, 68 g ai/ha or more, 69 g ai/ha ormore, 70 g ai/ha or more, 71 g ai/ha or more, 72 g ai/ha or more, 73 gai/ha or more, 74 g ai/ha or more, 75 g ai/ha or more, 76 g ai/ha ormore, or 77 g ai/ha or more,).

In some embodiments, the flumetsulam or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 78 g ai/ha or less (e.g., 77 g ai/ha or less,76 g ai/ha or less, 75 g ai/ha or less, 74 g ai/ha or less, 73 g ai/haor less, 72 g ai/ha or less, 71 g ai/ha or less, 70 g ai/ha or less, 69g ai/ha or less, 68 g ai/ha or less, 67 g ai/ha or less, 66 g ai/ha orless, 65 g ai/ha or less, 64 g ai/ha or less, 63 g ai/ha or less, 62 gai/ha or less, 61 g ai/ha or less, 60 g ai/ha or less, 59 g ai/ha orless, 58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha or less, 55 gai/ha or less, 54 g ai/ha or less, 53 g ai/ha or less, 52 g ai/ha orless, 51 g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 gai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha orless, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 gai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha orless, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 gai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha orless, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 gai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha orless, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 gai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha orless, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 gai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha orless, 9 g ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/haor less, 5 g ai/ha or less, 4.75 g ai/ha or less, 4.5 g ai/ha or less,4.25 g ai/ha or less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5 gai/ha or less, 3.25 g ai/ha or less, 3 g ai/ha or less, 2.75 g ai/ha orless, 2.5 g ai/ha or less, or 2.25 g ai/ha or less).

The flumetsulam or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the flumetsulamor agriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 2.18-78 g ai/ha (e.g.,2.5-75 g ai/ha, 2.75-70 g ai/ha, 3-65 g ai/ha, 3.25-78 g ai/ha, 3.5-75 gai/ha, 3.75-70 g ai/ha, 4-78 g ai/ha, 4-75 g ai/ha, 4-70 g ai/ha,4.25-78 g ai/ha, 4.25-75 g ai/ha, 4.25-70 g ai/ha, or 4.25-65 g ai/ha).

Penoxsulam

Compositions and methods of the present disclosure can includepenoxsulam or an agriculturally acceptable salt thereof. Penoxsulam,shown below, is a triazolopyrimidine sulfonamide that provides controlof Echinochloa spp., as well as many broadleaf, sedge, and aquatic weedsin rice. Penoxsulam, as well as methods of preparing penoxsulam, areknown in the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, penoxsulam can be provided as an agriculturallyacceptable salt of penoxsulam.

The penoxsulam or agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, thepenoxsulam or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.5 grams active ingredient per hectare (g ai/ha) or more (e.g., 2.75 gai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha ormore, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha ormore, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 gai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha ormore, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more,17 gai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha ormore, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 gai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha ormore, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 gai/ha or more, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha ormore, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 gai/ha or more, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha ormore, 42 g ai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 gai/ha or more, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha ormore, or 49 g ai/ha or more).

In some embodiments, the penoxsulam or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 50 g ai/ha or less (e.g., 49 g ai/ha or less,48 g ai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/haor less, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41g ai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha orless, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 gai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha orless, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 gai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha orless, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 gai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha orless, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 gai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha orless, 9 g ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/haor less, 5 g ai/ha or less, 4.75 g ai/ha or less, 4.5 g ai/ha or less,4.25 g ai/ha or less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5 gai/ha or less, 3.25 g ai/ha or less, 3 g ai/ha or less, or 2.75 g ai/haor less).

The penoxsulam or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the penoxsulamor agriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 2.5-50 g ai/ha (e.g.,3-48 g ai/ha, 3.25-46 g ai/ha, 3.5-40 g ai/ha, 3.5-50 g ai/ha, 3.75-45 gai/ha, 3.75-40 g ai/ha, 4-50 g ai/ha, 4-45 g ai/ha, 4-40 g ai/ha,4.25-50 g ai/ha, 4.25-48 g ai/ha, 4.25-46 g ai/ha, or 4.25-45 g ai/ha).

Pyroxsulam

Compositions and methods of the present disclosure can includepyroxsulam or an agriculturally acceptable salt thereof. Pyroxsulam,shown below, is a triazolopyrimidine sulfonamide that provides broadspectrum post-emergence annual grass and broadleaf weeds control incereals. Pyroxsulam, as well as methods of preparing pyroxsulam, areknown in the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, pyroxsulam can be provided as an agriculturallyacceptable salt of pyroxsulam.

The pyroxsulam or agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, thepyroxsulam or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of1.9 g ai/ha or more (e.g., 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/haor more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more,4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 gai/ha or more, 5.25 g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/haor more, 6 g ai/ha or more, 6.25 g ai/ha or more, 6.5 g ai/ha or more,6.75 g ai/ha or more, 7 g ai/ha or more, 7.25 g ai/ha or more, 7.5 gai/ha or more, 7.75 g ai/ha or more, 8 g ai/ha or more, 8.25 g ai/ha ormore, 8.5 g ai/ha or more, 8.75 g ai/ha or more, 9 g ai/ha or more, 9.25g ai/ha or more, 9.5 g ai/ha or more, 9.75 g ai/ha or more, 10 g ai/haor more, 10.25 g ai/ha or more, 10.5 g ai/ha or more, 10.75 g ai/ha ormore, 11 g ai/ha or more, 11.25 g ai/ha or more, 11.5 g ai/ha or more,11.75 g ai/ha or more, 12 g ai/ha or more, 12.25 g ai/ha or more, 12.5 gai/ha or more, 12.75 g ai/ha or more, 13 g ai/ha or more, 13.25 g ai/haor more, 13.5 g ai/ha or more, 13.75 g ai/ha or more, 14 g ai/ha ormore, 14.25 g ai/ha or more, 14.5 g ai/ha or more, 14.75 g ai/ha ormore, 15 g ai/ha or more, 15.25 g ai/ha or more, 15.5 g ai/ha or more,15.75 g ai/ha or more, 16 g ai/ha or more, 16.25 g ai/ha or more, 16.5 gai/ha or more, 16.75 g ai/ha or more, 17 g ai/ha or more, 17.25 g ai/haor more, 17.5 g ai/ha or more, 17.75 g ai/ha or more, 18 g ai/ha ormore, 18.25 g ai/ha or more, or 18.5 g ai/ha or more).

In some embodiments, the pyroxsulam or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 18.75 g ai/ha or less (e.g., 18.5 g ai/ha orless, 18.25 g ai/ha or less, 18 g ai/ha or less, 17.75 g ai/ha or less,17.5 g ai/ha or less, 17.25 g ai/ha or less, 17 g ai/ha or less, 16.75 gai/ha or less, 16.5 g ai/ha or less, 16.25 g ai/ha or less, 16 g ai/haor less, 15.75 g ai/ha or less, 15.5 g ai/ha or less, 15.25 g ai/ha orless, 15 g ai/ha or less, 14.75 g ai/ha or less, 14.5 g ai/ha or less,14.25 g ai/ha or less, 14 g ai/ha or less, 13.75 g ai/ha or less, 13.5 gai/ha or less, 13.25 g ai/ha or less, 13 g ai/ha or less, 12.75 g ai/haor less, 12.5 g ai/ha or less, 12.25 g ai/ha or less, 12 g ai/ha orless, 11.75 g ai/ha or less, 11.5 g ai/ha or less, 11.25 g ai/ha orless, 11 g ai/ha or less, 10.75 g ai/ha or less, 10.5 g ai/ha or less,10.25 g ai/ha or less, 10 g ai/ha or less, 9.75 g ai/ha or less, 9.5 gai/ha or less, 9.25 g ai/ha or less, 9 g ai/ha or less, 8.75 g ai/ha orless, 8.5 g ai/ha or less, 8.25 g ai/ha or less, 8 g ai/ha or less, 7.75g ai/ha or less, 7.5 g ai/ha or less,7.25 g ai/ha or less, 7 g ai/ha orless, 6.75 g ai/ha or less, 6.5 g ai/ha or less, 6.25 g ai/ha or less, 6g ai/ha or less, 5.75 g ai/ha or less, 5.5 g ai/ha or less, 5.25 g ai/haor less, 5 g ai/ha or less, 4.75 g ai/ha or less, 4.5 g ai/ha or less,4.25 g ai/ha or less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5 gai/ha or less, 3.25 g ai/ha or less, 3 g ai/ha or less, 2.75 g ai/ha orless, 2.5 g ai/ha or less, 2.25 g ai/ha or less, or 2 g ai/ha or less).

The pyroxsulam or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the pyroxsulamor agriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 1.9-18.75 g ai/ha(e.g., 2.5-18 g ai/ha, 2.5-17 g ai/ha, 2.75-16 g ai/ha, 2.75-18.75 gai/ha, 3-18 g ai/ha, 3.25-17 g ai/ha, 3.25-16 g ai/ha, 3.5-18.75 gai/ha, 3.5-18 g ai/ha, 3.5-17 g ai/ha, 3.5-16 g ai/ha, 3.5-15 g ai/ha,or 3.5-14 g ai/ha).

In certain embodiments, the herbicidal composition comprises aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof, and (b) imazamethabenz, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, agriculturally acceptable salts or estersthereof, or combinations thereof.

Imazamethabenz

Compositions and methods of the present disclosure can includeimazamethabenz or an agriculturally acceptable salt or ester thereof.Imazamethabenz, shown below, is a mixture of isomers and animidazolinone that provides post-emergence control of Avena species,Alopecurus myosuroides, Apera spica-venti and dicotyledonous weeds inwheat, barley, rye, and sunflowers. Imazamethabenz, as well as methodsof preparing imazamethabenz, are known in the art. Its herbicidalactivity is described in The Pesticide Manual, Fifteenth Edition, 2009.

In some embodiments, imazamethabenz can be provided as an agriculturallyacceptable salt or ester of imazamethabenz.

The imazamethabenz or agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount sufficient to induce a herbicidal effect. Insome embodiments, the imazamethabenz or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 50 g ai/ha or more (e.g., 55 gai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha ormore, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 gai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha ormore, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/haor more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more,220 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 gai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 280 g ai/ha ormore, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/haor more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more,390 g ai/ha or more, 400 g ai/ha or more, 410 g ai/ha or more, 420 gai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha ormore, 460 g ai/ha or more, 470 g ai/ha or more, 480 g ai/ha or more, 490g ai/ha or more, 500 g ai/ha or more, 510 g ai/ha or more, 520 g ai/haor more, 530 g ai/ha or more, 540 g ai/ha or more, 550 g ai/ha or more,560 g ai/ha or more, 570 g ai/ha or more, 580 g ai/ha or more, 590 gai/ha or more, 600 g ai/ha or more, 610 g ai/ha or more, 620 g ai/ha ormore, 630 g ai/ha or more, 640 g ai/ha or more, 650 g ai/ha or more, 660g ai/ha or more, 670 g ai/ha or more, 680 g ai/ha or more, or 690 gai/ha or more).

In some embodiments, the imazamethabenz or agriculturally acceptablesalt or ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 700 g ai/ha or less (e.g., 690 gai/ha or less, 680 g ai/ha or less, 670 g ai/ha or less, 660 g ai/ha orless, 650 g ai/ha or less, 640 g ai/ha or less, 630 g ai/ha or less, 620g ai/ha or less, 610 g ai/ha or less, 600 g ai/ha or less, 590 g ai/haor less, 580 g ai/ha or less, 570 g ai/ha or less, 560 g ai/ha or less,550 g ai/ha or less, 540 g ai/ha or less, 530 g ai/ha or less, 520 gai/ha or less, 510 g ai/ha or less, 500 g ai/ha or less, 490 g ai/ha orless, 480 g ai/ha or less, 470 g ai/ha or less, 460 g ai/ha or less, 450g ai/ha or less, 440 g ai/ha or less, 430 g ai/ha or less, 420 g ai/haor less, 410 g ai/ha or less, 400 g ai/ha or less, 390 g ai/ha or less,380 g ai/ha or less, 370 g ai/ha or less, 360 g ai/ha or less, 350 gai/ha or less, 340 g ai/ha or less, 330 g ai/ha or less, 320 g ai/ha orless, 310 g ai/ha or less, 300 g ai/ha or less, 290 g ai/ha or less, 280g ai/ha or less, 270 g ai/ha or less, 260 g ai/ha or less, 250 g ai/haor less, 240 g ai/ha or less, 230 g ai/ha or less, 220 g ai/ha or less,210 g ai/ha or less, 200 g ai/ha or less, 190 g ai/ha or less, 180 gai/ha or less, 170 g ai/ha or less, 160 g ai/ha or less, 150 g ai/ha orless, 140 g ai/ha or less, 130 g ai/ha or less, 120 g ai/ha or less, 110g ai/ha or less, 100 g ai/ha or less, 95 g ai/ha or less, 90 g ai/ha orless, 85 g ai/ha or less, 80 g ai/ha or less, 75 g ai/ha or less, 70 gai/ha or less, 65 g ai/ha or less, 60 g ai/ha or less, or 55 g ai/ha orless).

The imazamethabenz or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the imazamethabenz or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 50-700 g ai/ha (e.g., 50-400 g ai/ha, 400-700 g ai/ha, 50-650g ai/ha, 50-600 g ai/ha, 50-500 g ai/ha, 60-700 g ai/ha, 60-600 g ai/ha,60-500 g ai/ha, 70-700 g ai/ha, 70-600 g ai/ha, 70-500 g ai/ha, 70-400 gai/ha, or 100-500 g ai/ha).

Imazamox

Compositions and methods of the present disclosure can include imazamoxor an agriculturally acceptable salt thereof Imazamox, shown below, isan imidazolinone that provides pre- and post-emergence control ofbroadleaf and grass weeds, e.g., in rice, maize, rape, alfalfa, peas,and beans. Imazamox, as well as methods of preparing imazamox, are knownin the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, imazamox can be provided as an agriculturallyacceptable salt of imazamox.

The imazamox or agriculturally acceptable salt thereof can be applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, theimazamox or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of 5g ai/ha or more (e.g., 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/haor more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 gai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha ormore, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 gai/ha or more, 20 g ai/ha or more, 21 g ai/ha or more, 22 g ai/ha ormore, 23 g ai/ha or more, 24 g ai/ha or more, 25 g ai/ha or more, 26 gai/ha or more, 27 g ai/ha or more, 28 g ai/ha or more, 29 g ai/ha ormore, 30 g ai/ha or more, 31 g ai/ha or more, 32 g ai/ha or more, 33 gai/ha or more, 34 g ai/ha or more, 35 g ai/ha or more, 36 g ai/ha ormore, 37 g ai/ha or more, 38 g ai/ha or more, 39 g ai/ha or more, 40 gai/ha or more, 41 g ai/ha or more, 42 g ai/ha or more, 43 g ai/ha ormore, 44 g ai/ha or more, 45 g ai/ha or more, 46 g ai/ha or more, 47 gai/ha or more, 48 g ai/ha or more, 49 g ai/ha or more, 50 g ai/ha ormore, 51 g ai/ha or more, 52 g ai/ha or more, 53 g ai/ha or more, 54 gai/ha or more, 55 g ai/ha or more, 56 g ai/ha or more, 57 g ai/ha ormore, 58 g ai/ha or more, or 59 g ai/ha or more).

In some embodiments, the imazamox or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 60 g ai/ha or less (e.g., 59 g ai/ha or less,58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/haor less, 54 g ai/ha or less, 53 g ai/ha or less, 52 g ai/ha or less, 51g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha orless, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 gai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha orless, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 gai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha orless, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 gai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha orless, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 gai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha orless, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 gai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha orless, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, 9 gai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, or 6 g ai/ha orless).

The imazamox or an agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountranging from any of the minimum values described above to any of themaximum values described above. In some embodiments, the imazamox oragriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 5-60 g ai/ha (e.g.,5-58 g ai/ha, 5-56 g ai/ha, 5-54 g ai/ha, 5-52 g ai/ha, 5-50 g ai/ha,5-48 g ai/ha, 5-45 g ai/ha, 6-60 g ai/ha, 6-58 g ai/ha, 6-56 g ai/ha,6-54 g ai/ha, 7-60 g ai/ha, or 7-58 g ai/ha).

Imazapic

Compositions and methods of the present disclosure can include imazapicor an agriculturally acceptable salt or ester thereof. Imazapic, shownbelow, is an imidazolinone that provides pre- and post-emergence controlof a wide range of annual and perennial weeds in pasture, rangeland, andnon-cropland areas. Imazapic, as well as methods of preparing imazapic,are known in the art. Its herbicidal activity is described in ThePesticide Manual, Fifteenth Edition 2009.

In some embodiments, imazapic can be provided as an agriculturallyacceptable salt or ester of imazapic.

The imazapic or agriculturally acceptable salt or ester thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the imazapic or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of17.5 g ai/ha or more (e.g., 18 g ai/ha or more, 19 g ai/ha or more, 20 gai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha ormore, 24 g ai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 gai/ha or more, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha ormore, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 gai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha ormore, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 gai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha ormore, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 135 g ai/haor more, 140 g ai/ha or more, 145 g ai/ha or more, 150 g ai/ha or more,155 g ai/ha or more, 160 g ai/ha or more, 165 g ai/ha or more, 170 gai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 185 g ai/ha ormore, 190 g ai/ha or more, 195 g ai/ha or more, 200 g ai/ha or more, 205g ai/ha or more, 210 g ai/ha or more, or 215 g ai/ha or more).

In some embodiments, the imazapic or agriculturally acceptable salt orester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 220 g ai/ha or less (e.g., 215 gai/ha or less, 210 g ai/ha or less, 205 g ai/ha or less, 200 g ai/ha orless, 195 g ai/ha or less, 190 g ai/ha or less, 185 g ai/ha or less, 180g ai/ha or less, 175 g ai/ha or less, 170 g ai/ha or less, 165 g ai/haor less, 160 g ai/ha or less, 155 g ai/ha or less, 150 g ai/ha or less,145 g ai/ha or less, 140 g ai/ha or less, 135 g ai/ha or less, 130 gai/ha or less, 125 g ai/ha or less, 120 g ai/ha or less, 115 g ai/ha orless, 110 g ai/ha or less, 105 g ai/ha or less, 100 g ai/ha or less, 95g ai/ha or less, 90 g ai/ha or less, 85 g ai/ha or less, 80 g ai/ha orless, 75 g ai/ha or less, 70 g ai/ha or less, 65 g ai/ha or less, 60 gai/ha or less, 55 g ai/ha or less, 50 g ai/ha or less, 45 g ai/ha orless, 40 g ai/ha or less, 35 g ai/ha or less, 30 g ai/ha or less, 29 gai/ha or less, 28 g ai/ha or less, 27 g ai/ha or less, 26 g ai/ha orless, 25 g ai/ha or less, 24 g ai/ha or less, 23 g ai/ha or less, 22 gai/ha or less, 21 g ai/ha or less, 20 g ai/ha or less, 19 g ai/ha orless, or 18 g ai/ha or less).

The imazapic or an agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the imazapic oragriculturally acceptable salt or ester thereof is applied to vegetationor an area adjacent the vegetation or applied to soil or water toprevent the emergence or growth of vegetation in an amount of 17.5-220 gai/ha (e.g., 17.5-210 g ai/ha, 17.5-200 g ai/ha, 18-220 g ai/ha, 18-210g ai/ha, 18-200 g ai/ha, 18-190 g ai/ha, 20-220 g ai/ha, 20-210 g ai/ha,20-200 g ai/ha, 20-190 g ai/ha, 20-180 g ai/ha, 25-220 g ai/ha, or25-200 g ai/ha).

Imazapyr

Compositions and methods of the present disclosure can include imazapyror an agriculturally acceptable salt or ester thereof. Imazapyr, shownbelow, is an imidazolinone that provides pre- and post-emergence controlof annual and perennial grasses, broadleaf weeds, brush, and trees.Imazapyr, as well as methods of preparing imazapyr, are known in theart. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, imazapyr can be provided as an agriculturallyacceptable salt or ester of imazapyr.

The imazapyr or agriculturally acceptable salt or ester thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the imazapyr or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 140 g ai/ha or more (e.g., 145 g ai/ha or more, 150 g ai/ha ormore, 155 g ai/ha or more, 160 g ai/ha or more, 165 g ai/ha or more, 170g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/haor more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more,275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 gai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha ormore, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 550g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/haor more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more,900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 gai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/haor more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha ormore, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more,1550 g ai/ha or more, 1600 g ai/ha or more, 1620 g ai/ha or more, 1640 gai/ha or more, 1660 g ai/ha or more, or 1680 g ai/ha or more).

In some embodiments, the imazapyr or agriculturally acceptable salt orester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 1700 g ai/ha or less (e.g., 1680 gai/ha or less, 1660 g ai/ha or less, 1640 g ai/ha or less, 1620 g ai/haor less, 1600 g ai/ha or less, 1550 g ai/ha or less, 1500 g ai/ha orless, 1450 g ai/ha or less, 1400 g ai/ha or less, 1350 g ai/ha or less,1300 g ai/ha or less, 1250 g ai/ha or less, 1200 g ai/ha or less, 1150 gai/ha or less, 1100 g ai/ha or less, 1050 g ai/ha or less, 1000 g ai/haor less, 950 g ai/ha or less, 900 g ai/ha or less, 850 g ai/ha or less,800 g ai/ha or less, 750 g ai/ha or less, 700 g ai/ha or less, 650 gai/ha or less, 600 g ai/ha or less, 550 g ai/ha or less, 500 g ai/ha orless, 475 g ai/ha or less, 450 g ai/ha or less, 425 g ai/ha or less, 400g ai/ha or less, 375 g ai/ha or less, 350 g ai/ha or less, 325 g ai/haor less, 300 g ai/ha or less, 275 g ai/ha or less, 250 g ai/ha or less,225 g ai/ha or less, 200 g ai/ha or less, 190 g ai/ha or less, 180 gai/ha or less, 175 g ai/ha or less, 170 g ai/ha or less, 165 g ai/ha orless, 160 g ai/ha or less, 155 g ai/ha or less, 150 g ai/ha or less, or145 g ai/ha or less,).

The imazapyr or an agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the imazapyr oragriculturally acceptable salt or ester thereof is applied to vegetationor an area adjacent the vegetation or applied to soil or water toprevent the emergence or growth of vegetation in an amount of 140-1700 gai/ha (e.g., 140-850 g ai/ha, 850-1700 g ai/ha, 140-1600 g ai/ha,140-1500 g ai/ha, 140-1400 g ai/ha, 140-1200 g ai/ha, 140-1000 g ai/ha,150-1700 g ai/ha, 150-1500 g ai/ha, 150-1250 g ai/ha, 150-1000 g ai/ha,175-1500 g ai/ha, or 175-1000 g ai/ha).

Imazethapyr

Compositions and methods of the present disclosure can includeimazethapyr or an agriculturally acceptable salt or ester thereof.Imazethapyr, shown below, is an imidazolinone that controls many majorannual and perennial grass and broadleaf weeds in most major crops.Imazethapyr, as well as methods of preparing imazethapyr, are known inthe art. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, imazethapyr can be provided as an agriculturallyacceptable salt or ester of imazethapyr.

The imazethapyr or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the imazethapyr or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 8.75 g ai/ha or more (e.g., 9 g ai/ha or more, 9.5 g ai/ha ormore, 10 g ai/ha or more, 10.5 g ai/ha or more, 11 g ai/ha or more, 11.5g ai/ha or more, 12 g ai/ha or more, 12.5 g ai/ha or more, 13 g ai/ha ormore, 13.5 g ai/ha or more, 14 g ai/ha or more, 14.5 g ai/ha or more, 15g ai/ha or more, 15.5 g ai/ha or more, 16 g ai/ha or more, 16.5 g ai/haor more, 17 g ai/ha or more, 17.5 g ai/ha or more, 18 g ai/ha or more,18.5 g ai/ha or more, 19 g ai/ha or more, 19.5 g ai/ha or more, 20 gai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha ormore, 24 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 gai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha ormore, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 gai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha ormore, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/haor more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more,230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 gai/ha or more, 270 g ai/ha or more, 272 g ai/ha or more, 274 g ai/ha ormore, 276 g ai/ha or more, or 278 g ai/ha or more).

In some embodiments, the imazethapyr or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 280 g ai/ha or less (e.g., 278 gai/ha or less, 276 g ai/ha or less, 274 g ai/ha or less, 272 g ai/ha orless, 270 g ai/ha or less, 260 g ai/ha or less, 250 g ai/ha or less, 240g ai/ha or less, 230 g ai/ha or less, 220 g ai/ha or less, 210 g ai/haor less, 200 g ai/ha or less, 190 g ai/ha or less, 180 g ai/ha or less,170 g ai/ha or less, 160 g ai/ha or less, 150 g ai/ha or less, 140 gai/ha or less, 130 g ai/ha or less, 120 g ai/ha or less, 110 g ai/ha orless, 100 g ai/ha or less, 90 g ai/ha or less, 80 g ai/ha or less, 70 gai/ha or less, 60 g ai/ha or less, 50 g ai/ha or less, 45 g ai/ha orless, 40 g ai/ha or less, 35 g ai/ha or less, 30 g ai/ha or less, 25 gai/ha or less, 24 g ai/ha or less, 23 g ai/ha or less, 22 g ai/ha orless, 21 g ai/ha or less, 20 g ai/ha or less, 19.5 g ai/ha or less, 19 gai/ha or less, 18.5 g ai/ha or less, 18 g ai/ha or less, 17.5 g ai/ha orless, 17 g ai/ha or less, 16.5 g ai/ha or less, 16 g ai/ha or less, 15.5g ai/ha or less, 15 g ai/ha or less, 14.5 g ai/ha or less, 14 g ai/ha orless, 13.5 g ai/ha or less, 13 g ai/ha or less, 12.5 g ai/ha or less, 12g ai/ha or less, 11.5 g ai/ha or less, 11 g ai/ha or less, 10.5 g ai/haor less, 10 g ai/ha or less, 9.5 g ai/ha or less, or 9 g ai/ha or less).

The imazethapyr or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the imazethapyr or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 8.75-280 g ai/ha (e.g., 8.75-275 g ai/ha, 8.75-270 g ai/ha,8.75-260 g ai/ha, 8.75-250 g ai/ha, 8.75-225 g ai/ha, 8.75-200 g ai/ha,10-280 g ai/ha, 10-250 g ai/ha, 10-200 g ai/ha, 15-280 g ai/ha, 15-250 gai/ha, 15-200 g ai/ha, or 17.5-250 g ai/ha).

In certain embodiments, the herbicidal composition comprises aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof, and (b) bispyribac, pyribenzoxim, pyriftalid, pyriminobac,pyrimisulfan, pyrithiobac, agriculturally acceptable salts or estersthereof, or combinations thereof.

Bispyribac

Compositions and methods of the present disclosure can includebispyribac or an agriculturally acceptable salt thereof.Bispyribac-sodium, shown below, is a pyrimidinyl oxybenzoate thatprovides control of grasses, sedges, and broadleaf weeds, e.g., indirect-seeded and water-seeded rice and in turf. Bispyribac-sodium, aswell as methods of preparing bispyribac-sodium, are known in the art.Its herbicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009.

The bispyribac or agriculturally acceptable salt thereof can be appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amountsufficient to induce a herbicidal effect. In some embodiments, thebispyribac or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of 5g ai/ha or more (e.g., 5.5 g ai/ha or more, 6 g ai/ha or more, 6.5 gai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha ormore, 8.5 g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha or more, 10 gai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha ormore, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 gai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha ormore, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 gai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha ormore, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 gai/ha or more, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha ormore, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 gai/ha or more, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha ormore, 42 g ai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 gai/ha or more, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha ormore, 49 g ai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 gai/ha or more, 53 g ai/ha or more, 54 g ai/ha or more, 55 g ai/ha ormore, 56 g ai/ha or more, 57 g ai/ha or more, 58 g ai/ha or more, or 59g ai/ha or more).

In some embodiments, the bispyribac or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 60 g ai/ha or less (e.g., 59 g ai/ha or less,58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/haor less, 54 g ai/ha or less, 53g ai/ha or less, 52 g ai/ha or less, 51 gai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha orless, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 gai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha orless, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 gai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha orless, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 gai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha orless, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 gai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha orless, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 gai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha orless, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, 9.5 gai/ha or less, 9 g ai/ha or less, 8.5 g ai/ha or less, 8 g ai/ha orless, 7.5 g ai/ha or less, 7 g ai/ha or less, 6.5 g ai/ha or less, 6 gai/ha or less, or 5.5 g ai/ha or less,).

The bispyribac or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the bispyribacor agriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 5-60 g ai/ha (e.g.,5-58 g ai/ha, 5-56 g ai/ha, 5-54 g ai/ha, 5-52 g ai/ha, 5-50 g ai/ha,6-60 g ai/ha, 6-58 g ai/ha, 6-56 g ai/ha, 6-55 g ai/ha, 7.5-60 g ai/ha,7.5-55 g ai/ha, 7.5-50 g ai/ha, or 8-50 g ai/ha).

Pyribenzoxim

Compositions and methods of the present disclosure can includepyribenzoxim. Pyribenzoxim, shown below, is a pyrimidinyl oxybenzoatethat provides post-emergence control of barnyard grass, blackgrass, andpolygonums, e.g., in rice, wheat, and zoysiagrass. Pyribenzoxim, as wellas methods of preparing pyribenzoxim, are known in the art. Itsherbicidal activity is described, for example, in The Pesticide Manual,Fifteenth Edition, 2009.

The pyribenzoxim or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the pyribenzoxim or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of7.5 g ai/ha or more (e.g., 7.75 g ai/ha or more, 8 g ai/ha or more, 8.5g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha or more, 10 g ai/ha ormore, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 gai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha ormore, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 21 gai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 g ai/ha ormore, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha or more, 28 gai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 g ai/ha ormore, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha or more, 35 gai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 g ai/ha ormore, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha or more, 42 gai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 g ai/ha ormore, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha or more, 49 gai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 g ai/ha ormore, 53 g ai/ha or more, 54 g ai/ha or more, 55 g ai/ha or more, 56 gai/ha or more, 57 g ai/ha or more, 58 g ai/ha or more, 59 g ai/ha ormore, 60 g ai/ha or more, 61 g ai/ha or more, 62 g ai/ha or more, 63 gai/ha or more, 64 g ai/ha or more, 65 g ai/ha or more, 66 g ai/ha ormore, 67 g ai/ha or more, 68 g ai/ha or more, or 69 g ai/ha or more).

In some embodiments, the pyribenzoxim or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 70 g ai/ha or less (e.g., 69 g ai/ha or less,68 g ai/ha or less, 67 g ai/ha or less, 66 g ai/ha or less, 65 g ai/haor less, 64 g ai/ha or less, 63 g ai/ha or less, 62 g ai/ha or less, 61g ai/ha or less, 60 g ai/ha or less, 59 g ai/ha or less, 58 g ai/ha orless, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/ha or less, 54 gai/ha or less, 53 g ai/ha or less, 52 g ai/ha or less, 51 g ai/ha orless, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha or less, 47 gai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 g ai/ha orless, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha or less, 40 gai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 g ai/ha orless, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha or less, 33 gai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 g ai/ha orless, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha or less, 26 gai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 g ai/ha orless, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha or less, 19 gai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 g ai/ha orless, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha or less, 12 gai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, 9.5 g ai/ha orless, 9 g ai/ha or less, 8.5 g ai/ha or less, 8 g ai/ha or less, or 7.75g ai/ha or less).

The pyribenzoxim or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thepyribenzoxim is applied to vegetation or an area adjacent the vegetationor applied to soil or water to prevent the emergence or growth ofvegetation in an amount of 7.5-70 g ai/ha (e.g., 7.5-68 g ai/ha, 7.5-65g ai/ha, 7.75-60 g ai/ha, 9-70 g ai/ha, 9-68 g ai/ha, 9-65 g ai/ha, 9-60g ai/ha, 10-70 g ai/ha, 10-68 g ai/ha, 10-65 g ai/ha, 10-60 g ai/ha,20-60 g ai/ha, or 20-50 g ai/ha).

In certain embodiments, the herbicidal composition comprises aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof, and (b) flucarbazone, propoxycarbazone, thiencarbazone,agriculturally acceptable salts or esters thereof, or combinationsthereof.

Flucarbazone

Compositions and methods of the present disclosure can includeflucarbazone or an agriculturally acceptable salt thereof. Flucarbazone,shown below, is a sulfonylamino-carbonyl triazolinone that providespost-emergence control of annual grass weeds and some perennial grassweeds and some broad-leaved weeds. Flucarbazone, as well as methods ofpreparing flucarbazone, are known in the art. Its herbicidal activity isdescribed in The Pesticide Manual, Fifteenth Edition, 2009.

In some embodiments, flucarbazone can be provided as an agriculturallyacceptable salt of flucarbazone.

The flucarbazone or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the flucarbazone or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.75 g ai/ha or more (e.g., 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g ai/haor more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more,6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/haor more, 8.5 g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha or more, 10g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 12.5 g ai/ha ormore, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 gai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha ormore, 20 g ai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 gai/ha or more, 24 g ai/ha or more, 25 g ai/ha or more, 25.5 g ai/ha ormore, 26 g ai/ha or more, 26.5 g ai/ha or more, 27 g ai/ha or more, 27.5g ai/ha or more, 28 g ai/ha or more, 28.5 g ai/ha or more, 29 g ai/ha ormore, 29.25 g ai/ha or more, 29.5 g ai/ha or more, or 29.75 g ai/ha ormore).

In some embodiments, the flucarbazone or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 30 g ai/ha or less (e.g., 29.75 g ai/ha orless, 29.5 g ai/ha or less, 29.25 g ai/ha or less, 29 g ai/ha or less,28.5 g ai/ha or less, 28 g ai/ha or less, 27.5 g ai/ha or less, 27 gai/ha or less, 26.5 g ai/ha or less, 26 g ai/ha or less, 25 g ai/ha orless, 24 g ai/ha or less, 23 g ai/ha or less, 22 g ai/ha or less, 21 gai/ha or less, 20 g ai/ha or less, 19 g ai/ha or less, 18 g ai/ha orless, 17 g ai/ha or less, 16 g ai/ha or less, 15 g ai/ha or less, 14 gai/ha or less, 13 g ai/ha or less, 12 g ai/ha or less, 11 g ai/ha orless, 10 g ai/ha or less, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5 gai/ha or less, 8 g ai/ha or less, 7.5 g ai/ha or less, 7 g ai/ha orless, 6.5 g ai/ha or less, 6 g ai/ha or less, 5.75 g ai/ha or less, 5.5g ai/ha or less, 5.25 g ai/ha or less, 5 g ai/ha or less, 4.75 g ai/haor less, 4.5 g ai/ha or less, 4.25 g ai/ha or less, or 4 g ai/ha orless).

The flucarbazone or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, theflucarbazone or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.75-30 g ai/ha (e.g., 3.75-29 g ai/ha, 3.75-28 g ai/ha, 3.75-27 gai/ha, 3.75-25 g ai/ha, 4-30 g ai/ha, 4-28 g ai/ha, 4-26 g ai/ha, 4-25 gai/ha, 5-30 g ai/ha, 5-28 g ai/ha, 5-25 g ai/ha, 6-30 g ai/ha, or 6-25 gai/ha).

Propoxycarbazone

Compositions and methods of the present disclosure can includepropoxycarbazone or an agriculturally acceptable salt thereof.Propoxycarbazone, shown below, is a sulfonylaminocarbonyl triazolinonethat provides post-emergence control of grass weeds and somebroad-leaved weeds. Propoxycarbazone, as well as methods of preparingpropoxycarbazone, are known in the art. Its herbicidal activity isdescribed in The Pesticide Manual, Fifteenth Edition, 2009.

In some embodiments, propoxycarbazone can be provided as anagriculturally acceptable salt of propoxycarbazone.

The propoxycarbazone or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the propoxycarbazone or agriculturally acceptable salt thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 3.75 g ai/ha or more (e.g., 4 g ai/ha or more, 4.25 g ai/ha ormore, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.5g ai/ha or more, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha ormore, 7.5 g ai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 gai/ha or more, 9.5 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha ormore, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 gai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha ormore, 19 g ai/ha or more, 20 g ai/ha or more, 21 g ai/ha or more, 22 gai/ha or more, 23 g ai/ha or more, 24 g ai/ha or more, 25 g ai/ha ormore, 26 g ai/ha or more, 27 g ai/ha or more, 28 g ai/ha or more, 29 gai/ha or more, 30 g ai/ha or more, 31 g ai/ha or more, 32 g ai/ha ormore, 33 g ai/ha or more, 34 g ai/ha or more, 35 g ai/ha or more, 36 gai/ha or more, 37 g ai/ha or more, 38 g ai/ha or more, 39 g ai/ha ormore, 40 g ai/ha or more, 41 g ai/ha or more, 42 g ai/ha or more, 43 gai/ha or more, 44 g ai/ha or more, 45 g ai/ha or more, 46 g ai/ha ormore, 47 g ai/ha or more, 48 g ai/ha or more, 49 g ai/ha or more, 50 gai/ha or more, 51 g ai/ha or more, 52 g ai/ha or more, 53 g ai/ha ormore, 54 g ai/ha or more, 55 g ai/ha or more, 56 g ai/ha or more, 57 gai/ha or more, 58 g ai/ha or more, 59 g ai/ha or more, 60 g ai/ha ormore, 61 g ai/ha or more, 62 g ai/ha or more, 63 g ai/ha or more, 64 gai/ha or more, 65 g ai/ha or more, 66 g ai/ha or more, 67 g ai/ha ormore, 68 g ai/ha or more, or 69 g ai/ha or more).

In some embodiments, the propoxycarbazone or agriculturally acceptablesalt thereof is applied to vegetation or an area adjacent the vegetationor applied to soil or water to prevent the emergence or growth ofvegetation in an amount of 70 g ai/ha or less (e.g., 69 g ai/ha or less,68 g ai/ha or less, 67 g ai/ha or less, 66 g ai/ha or less, 65 g ai/haor less, 64 g ai/ha or less, 63 g ai/ha or less, 62 g ai/ha or less, 61g ai/ha or less, 60 g ai/ha or less, 59 g ai/ha or less, 58 g ai/ha orless, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/ha or less, 54 gai/ha or less, 53 g ai/ha or less, 52 g ai/ha or less, 51 g ai/ha orless, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha or less, 57 gai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 g ai/ha orless, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha or less, 40 gai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 g ai/ha orless, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha or less, 33 gai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 g ai/ha orless, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha or less, 26 gai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 g ai/ha orless, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha or less, 19 gai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 g ai/ha orless, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha or less, 12 gai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, 9.5 g ai/ha orless, 9 g ai/ha or less, 8.5 g ai/ha or less, 8 g ai/ha or less, 7.5 gai/ha or less, 7 g ai/ha or less, 6.5 g ai/ha or less, 6 g ai/ha orless, 5.5 g ai/ha or less, 5 g ai/ha or less, 4.75 g ai/ha or less, 4.5g ai/ha or less, 4.25 g ai/ha or less, or 4 g ai/ha or less).

The propoxycarbazone or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thepropoxycarbazone or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.75-70 g ai/ha (e.g., 3.75-68 g ai/ha, 3.75-66 g ai/ha, 3.75-64 gai/ha, 3.75-62 g ai/ha, 3.75-60 g ai/ha, 4-70 g ai/ha, 4-65 g ai/ha,4-60 g ai/ha, 5-70 g ai/ha, 5-65 g ai/ha, 5-60 g ai/ha, 5-50 g ai/ha, or7.5-50 g ai/ha).

Thiencarbazone

Compositions and methods of the present disclosure can includethiencarbazone or an agriculturally acceptable salt or ester thereof.Thiencarbazone-methyl, shown below, is a sulfonylaminocarbonyltriazolinone that provides post-emergence control of grass weeds andsome broad-leaved weeds. Thiencarbazone, as well as methods of preparingthiencarbazone, are known in the art. Its herbicidal activity isdescribed in The Pesticide Manual, Fifteenth Edition, 2009.

In some embodiments, thiencarbazone can be provided as an agriculturallyacceptable salt or ester of thiencarbazone.

The thiencarbazone or agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount sufficient to induce a herbicidal effect. Insome embodiments, the thiencarbazone or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 2.5 g ai/ha or more (e.g., 2.75 gai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha ormore, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.5 g ai/ha ormore, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 gai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha ormore, 9.5 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 gai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha ormore, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 gai/ha or more, 20 g ai/ha or more, 21 g ai/ha or more, 22 g ai/ha ormore, 23 g ai/ha or more, 24 g ai/ha or more, 25 g ai/ha or more, 26 gai/ha or more, 27 g ai/ha or more, 28 g ai/ha or more, 29 g ai/ha ormore, 30 g ai/ha or more, 31 g ai/ha or more, 32 g ai/ha or more, 33 gai/ha or more, 34 g ai/ha or more, 35 g ai/ha or more, 36 g ai/ha ormore, 37 g ai/ha or more, 38 g ai/ha or more, 39 g ai/ha or more, 40 gai/ha or more, 41 g ai/ha or more, 42 g ai/ha or more, 43 g ai/ha ormore, or 44 g ai/ha or more).

In some embodiments, the thiencarbazone or agriculturally acceptablesalt thereof is applied to vegetation or an area adjacent the vegetationor applied to soil or water to prevent the emergence or growth ofvegetation in an amount of 45 g ai/ha or less (e.g., 44 g ai/ha or less,43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha or less, 40 g ai/haor less, 39 g ai/ha or less, 38 g ai/ha or less, 37 g ai/ha or less, 36g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha or less, 33 g ai/ha orless, 32 g ai/ha or less, 31 g ai/ha or less, 30 g ai/ha or less, 29 gai/ha or less, 28 g ai/ha or less, 27 g ai/ha or less, 26 g ai/ha orless, 25 g ai/ha or less, 24 g ai/ha or less, 23 g ai/ha or less, 22 gai/ha or less, 21 g ai/ha or less, 20 g ai/ha or less, 19 g ai/ha orless, 18 g ai/ha or less, 17 g ai/ha or less, 16 g ai/ha or less, 15 gai/ha or less, 14 g ai/ha or less, 13 g ai/ha or less, 12 g ai/ha orless, 11 g ai/ha or less, 10 g ai/ha or less, 9.5 g ai/ha or less, 9 gai/ha or less, 8.5 g ai/ha or less, 8 g ai/ha or less, 7.5 g ai/ha orless, 7 g ai/ha or less, 6.5 g ai/ha or less, 6 g ai/ha or less, 5.5 gai/ha or less, 5 g ai/ha or less, 4.75 g ai/ha or less, 4.5 g ai/ha orless, 4.25 g ai/ha or less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5g ai/ha or less, 3.25 g ai/ha or less, 3 g ai/ha or less, or 2.75 gai/ha or less).

The thiencarbazone or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thethiencarbazone or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.5-45 g ai/ha (e.g., 2.5-42 g ai/ha, 2.5-40 g ai/ha, 2.75-45 g ai/ha,2.75-40 g ai/ha, 3-45 g ai/ha, 3.25-45 g ai/ha, 3.25-40 g ai/ha, 3.5-45g ai/ha, 3.5-40 g ai/ha, 3.5-35 g ai/ha, 3.75-45 g ai/ha, 3.75-40 gai/ha, or 5-40 g ai/ha).

In certain embodiments, the herbicidal composition comprises aherbicidally effective amount of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof, and (b) amidosulfuron, azimsulfuron, bensulfuron, chlorimuron,chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron,ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron,mesosulfuron, metazosulfuron, metsulfuron, nicosulfuron,orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron,prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron,triasulfuron, tribenuron, thifensulfuron, trifloxysulfuron,triflusulfuron, tritosulfuron, agriculturally acceptable salts or estersthereof, or combinations thereof.

Amidosulfuron

Compositions and methods of the present disclosure can includeamidosulfuron or an agriculturally acceptable salt thereof.Amidosulfuron, shown below, is a sulfonylurea that providespost-emergence control of a wide range of broadleaf weeds, e.g.,cleavers, in winter wheat, durum wheat, barley, rye, triticale, andoats. Amidosulfuron, as well as methods of preparing amidosulfuron, areknown in the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, amidosulfuron can be provided as an agriculturallyacceptable salt of amidosulfuron.

The amidosulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the amidosulfuron or agriculturally acceptable salt thereof is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.75 g ai/ha or more (e.g., 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.5 g ai/ha ormore, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 gai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha ormore, 9.5 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 gai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha ormore, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 gai/ha or more, 20 g ai/ha or more, 21 g ai/ha or more, 22 g ai/ha ormore, 23 g ai/ha or more, 24 g ai/ha or more, 25 g ai/ha or more, 26 gai/ha or more, 27 g ai/ha or more, 28 g ai/ha or more, 29 g ai/ha ormore, 30 g ai/ha or more, 31 g ai/ha or more, 32 g ai/ha or more, 33 gai/ha or more, 34 g ai/ha or more, 35 g ai/ha or more, 36 g ai/ha ormore, 37 g ai/ha or more, 38 g ai/ha or more, 39 g ai/ha or more, 40 gai/ha or more, 41 g ai/ha or more, 42 g ai/ha or more, 43 g ai/ha ormore, 44 g ai/ha or more, 45 g ai/ha or more, 46 g ai/ha or more, 47 gai/ha or more, 48 g ai/ha or more, 49 g ai/ha or more, 50 g ai/ha ormore, 51 g ai/ha or more, 52 g ai/ha or more, 53 g ai/ha or more, 54 gai/ha or more, 55 g ai/ha or more, 56 g ai/ha or more, 57 g ai/ha ormore, 58 g ai/ha or more, or 59 g ai/ha or more).

In some embodiments, the amidosulfuron or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 60 g ai/ha or less (e.g., 59 g ai/ha or less,58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/haor less, 54 g ai/ha or less, 53 g ai/ha or less, 52 g ai/ha or less, 51g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha orless, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 gai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha orless, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 gai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha orless, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 gai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha orless, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 gai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha orless, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 gai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha orless, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, 9.5 gai/ha or less, 9 g ai/ha or less, 8.5 g ai/ha or less, 8 g ai/ha orless, 7.5 g ai/ha or less, 7 g ai/ha or less, 6.5 g ai/ha or less, 6 gai/ha or less, 5.5 g ai/ha or less, 5 g ai/ha or less, 4.75 g ai/ha orless, 4.5 g ai/ha or less, 4.25 g ai/ha or less, or 4 g ai/ha or less).

The amidosulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, theamidosulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.75-60 g ai/ha (e.g., 3.75-58 g ai/ha, 3.75-55 g ai/ha, 3.75-50 gai/ha, 4-60 g ai/ha, 4-55 g ai/ha, 4-50 g ai/ha, 4.25-60 g ai/ha,4.25-55 g ai/ha, 4.25-50 g ai/ha, 4.5-60 g ai/ha, 4.5-55 g ai/ha, 4.5-50g ai/ha, or 5-50 g ai/ha).

Azimsulfuron

Compositions and methods of the present disclosure can includeazimsulfuron or an agriculturally acceptable salt thereof. Azimsulfuron,shown below, is a sulfonylurea that provides e.g., post-emergencecontrol of annual and perennial broadleaf and sedge weeds in rice.Azimsulfuron, as well as methods of preparing azimsulfuron, are known inthe art. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, azimsulfuron can be provided as an agriculturallyacceptable salt of azimsulfuron.

The azimsulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the azimsulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.125 g ai/ha or more (e.g., 3.25 g ai/ha or more, 3.5 g ai/ha or more,3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 gai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.5 g ai/ha ormore, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 gai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha ormore, 9.5 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 gai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha ormore, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 gai/ha or more, 20 g ai/ha or more, 20.5 g ai/ha or more, 21 g ai/ha ormore, 21.5 g ai/ha or more, 22 g ai/ha or more, 22.5 g ai/ha or more,22.75 g ai/ha or more, 23 g ai/ha or more, 23.25 g ai/ha or more, 23.5 gai/ha or more, 23.75 g ai/ha or more, 24 g ai/ha or more, 24.25 g ai/haor more, 24.5 g ai/ha or more, or 24.75 g ai/ha or more).

In some embodiments, the azimsulfuron or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 25 g ai/ha or less (e.g., 24.75 g ai/ha orless, 24.5 g ai/ha or less, 24.25 g ai/ha or less, 24 g ai/ha or less,23.75 g ai/ha or less, 23.5 g ai/ha or less, 23.25 g ai/ha or less, 23 gai/ha or less, 22.75 g ai/ha or less, 22.5 g ai/ha or less, 22 g ai/haor less, 21.5 g ai/ha or less, 21 g ai/ha or less, 20.5 g ai/ha or less,20 g ai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/haor less, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13g ai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha orless, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5 g ai/ha or less, 8 gai/ha or less, 7.5 g ai/ha or less, 7 g ai/ha or less, 6.5 g ai/ha orless, 6 g ai/ha or less, 5.5 g ai/ha or less, 5 g ai/ha or less, 4.75 gai/ha or less, 4.5 g ai/ha or less, 4.25 g ai/ha or less, 4 g ai/ha orless, 3.75 g ai/ha or less, 3.5 g ai/ha or less, or 3.25 g ai/ha orless).

The azimsulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, theazimsulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of3.125-25 g ai/ha (e.g., 3.125-24 g ai/ha, 3.125-23 g ai/ha, 3.125-22 gai/ha, 3.125-20 g ai/ha, 3.5-25 g ai/ha, 3.5-22 g ai/ha, 3.5-20 g ai/ha,4-25 g ai/ha, 4-22 g ai/ha, 4-20 g ai/ha, 4.5-25 g ai/ha, 4.5-20 gai/ha, or 5-20 g ai/ha).

Bensulfuron

Compositions and methods of the present disclosure can includebensulfuron or an agriculturally acceptable salt or ester thereof.Bensulfuron-methyl, shown below, is a sulfonylurea that provides e.g.,pre- and post-emergence control of annual and perennial broadleaf weedsand sedges in rice. Bensulfuron, as well as methods of preparingbensulfuron, are known in the art. Its herbicidal activity is describedin The Pesticide Manual, Fifteenth Edition, 2009.

In certain embodiments, the free carboxylic acid, with respect to themethyl ester moiety, i.e.,α-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluic acid, or itssalt, is utilized. In certain embodiments, a different ester, e.g., analkyl or aralkyl ester is utilized.

The bensulfuron or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the bensulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 8.75 g ai/ha or more (e.g., 9 g ai/ha or more, 10 g ai/ha ormore, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 gai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha ormore, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 21 gai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 g ai/ha ormore, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha or more, 28 gai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 g ai/ha ormore, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha or more, 35 gai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 g ai/ha ormore, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha or more, 42 gai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 g ai/ha ormore, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha or more, 49 gai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 g ai/ha ormore, 53 g ai/ha or more, 54 g ai/ha or more, 55 g ai/ha or more, 56 gai/ha or more, 57 g ai/ha or more, 58 g ai/ha or more, 59 g ai/ha ormore, 60 g ai/ha or more, 61 g ai/ha or more, 62 g ai/ha or more, 63 gai/ha or more, 64 g ai/ha or more, 65 g ai/ha or more, 66 g ai/ha ormore, 67 g ai/ha or more, 68 g ai/ha or more, or 69 g ai/ha or more).

In some embodiments, the bensulfuron or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 70 g ai/ha or less (e.g., 69 gai/ha or less, 68 g ai/ha or less, 67 g ai/ha or less, 66 g ai/ha orless, 65 g ai/ha or less, 64 g ai/ha or less, 63 g ai/ha or less, 62 gai/ha or less, 61 g ai/ha or less, 60 g ai/ha or less, 59 g ai/ha orless, 58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha or less, 55 gai/ha or less, 54 g ai/ha or less, 53 g ai/ha or less, 52 g ai/ha orless, 51 g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 gai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha orless, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 gai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha orless, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 gai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha orless, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 gai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha orless, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 gai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha orless, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 gai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha orless, or 9 g ai/ha or less).

The bensulfuron or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the bensulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 8.75-70 g ai/ha (e.g., 8.75-68 g ai/ha, 8.75-65 g ai/ha, 9-60g ai/ha, 10-70 g ai/ha, 10-68 g ai/ha, 10-65 g ai/ha, 10-60 g ai/ha,11-70 g ai/ha, 11-68 g ai/ha, 11-65 g ai/ha, 11-60 g ai/ha, 20-60 gai/ha, or 20-50 g ai/ha).

Chlorsulfuron

Compositions and methods of the present disclosure can includechlorsulfuron or an agriculturally acceptable salt thereof.Chlorsulfuron, shown below, is a sulfonylurea that provides control ofe.g., broadleaf weeds and annual grasses in wheat, barley, oats, rye,triticale, flax, and on non-crop land. Chlorsulfuron, as well as methodsof preparing chlorsulfuron, are known in the art. Its herbicidalactivity is described in The Pesticide Manual, Fifteenth Edition, 2009.

In some embodiments, chlorsulfuron can be provided as an agriculturallyacceptable salt of chlorsulfuron.

The chlorsulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the chlorsulfuron or agriculturally acceptable salt thereof is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of1.1 g ai/ha or more (e.g., 1.25 g ai/ha or more, 1.5 g ai/ha or more,1.75 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 gai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha ormore, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha ormore, 5.5 g ai/ha or more, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 gai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha ormore, 9 g ai/ha or more, 9.5 g ai/ha or more, 10 g ai/ha or more, 11 gai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha ormore, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 gai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 21 g ai/ha ormore, 22 g ai/ha or more, 23 g ai/ha or more, 24 g ai/ha or more, 25 gai/ha or more, 26 g ai/ha or more, 27 g ai/ha or more, 28 g ai/ha ormore, 29 g ai/ha or more, 30 g ai/ha or more, 31 g ai/ha or more, 32 gai/ha or more, 33 g ai/ha or more, 34 g ai/ha or more, 25 g ai/ha ormore, 36 g ai/ha or more, 37 g ai/ha or more, 38 g ai/ha or more, 39 gai/ha or more, 40 g ai/ha or more, 41 g ai/ha or more, 42 g ai/ha ormore, 43 g ai/ha or more, 44 g ai/ha or more, 45 g ai/ha or more, 46 gai/ha or more, 47 g ai/ha or more, 48 g ai/ha or more, 49 g ai/ha ormore, 50 g ai/ha or more, 51 g ai/ha or more, or 51.5 g ai/ha or more).

In some embodiments, the chlorsulfuron or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 52 g ai/ha or less (e.g., 51.5 g ai/ha orless, 51 g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 gai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha orless, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 gai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha orless, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 gai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha orless, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 gai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha orless, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 gai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha orless, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 gai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha orless, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5 g ai/ha or less, 8 gai/ha or less, 7.5 g ai/ha or less, 7 g ai/ha or less, 6.5 g ai/ha orless, 6 g ai/ha or less, 5.5 g ai/ha or less, 5 g ai/ha or less, 4.75 gai/ha or less, 4.5 g ai/ha or less, or 4.25 g ai/ha or less, 4 g ai/haor less, 3.75 g ai/ha or less, 3.5 g ai/ha or less, 3.25 g ai/ha orless, 3 g ai/ha or less, 2.75 g ai/ha or less, 2.5 g ai/ha or less, 2.25g ai/ha or less, 2 g ai/ha or less, 1.75 g ai/ha or less, 1.5 g ai/ha orless, or 1.25 g ai/ha or less).

The chlorsulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thechlorsulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of1.1-52 g ai/ha (e.g., 1.1-52 g ai/ha, 1.1-50 g ai/ha, 1.5-52 g ai/ha,1.5-50 g ai/ha, 2-52 g ai/ha, 2-50 g ai/ha, 2.5-52 g ai/ha, 2.5-52 gai/ha, 3-52 g ai/ha, 3-50 g ai/ha, 3-45 g ai/ha, 3.5-52 g ai/ha, or3.5-50 g ai/ha).

Ethoxysulfuron

Compositions and methods of the present disclosure can includeethoxysulfuron or an agriculturally acceptable salt thereof.Ethoxysulfuron, shown below, is a sulfonylurea that provides, e.g.,control of broadleaf and sedge weeds in cereals, rice, and sugar cane.Ethoxysulfuron, as well as methods of preparing ethoxysulfuron, areknown in the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, ethoxysulfuron can be provided as an agriculturallyacceptable salt of ethoxysulfuron.

The ethoxysulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the ethoxysulfuron or agriculturally acceptable salt thereof is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of 5g ai/ha or more (e.g., 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/haor more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 gai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha ormore, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 gai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha ormore, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 gai/ha or more, 34 g ai/ha or more, 36 g ai/ha or more, 38 g ai/ha ormore, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 gai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha ormore, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 gai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 101 g ai/ha ormore, 102 g ai/ha or more, 103 g ai/ha or more, 104 g ai/ha or more, 105g ai/ha or more, 106 g ai/ha or more, 107 g ai/ha or more, 108 g ai/haor more, 109 g ai/ha or more, 110 g ai/ha or more, 111 g ai/ha or more,112 g ai/ha or more, 113 g ai/ha or more, 114 g ai/ha or more, 115 gai/ha or more, 116 g ai/ha or more, 117 g ai/ha or more, 118 g ai/ha ormore, or 119 g ai/ha or more).

In some embodiments, the ethoxysulfuron or agriculturally acceptablesalt thereof is applied to vegetation or an area adjacent the vegetationor applied to soil or water to prevent the emergence or growth ofvegetation in an amount of 120 g ai/ha or less (e.g., 119 g ai/ha orless, 118 g ai/ha or less, 117 g ai/ha or less, 116 g ai/ha or less, 115g ai/ha or less, 114 g ai/ha or less, 113g ai/ha or less, 112 g ai/ha orless, 111 g ai/ha or less, 110 g ai/ha or less, 109 g ai/ha or less, 108g ai/ha or less, 107 g ai/ha or less, 106 g ai/ha or less, 105 g ai/haor less, 104 g ai/ha or less, 103 g ai/ha or less, 102 g ai/ha or less,101 g ai/ha or less, 100 g ai/ha or less, 95 g ai/ha or less, 90 g ai/haor less, 85 g ai/ha or less, 80 g ai/ha or less, 75 g ai/ha or less, 70g ai/ha or less, 65 g ai/ha or less, 60 g ai/ha or less, 55 g ai/ha orless, 50 g ai/ha or less, 45 g ai/ha or less, 40 g ai/ha or less, 38 gai/ha or less, 36 g ai/ha or less, 34 g ai/ha or less, 32 g ai/ha orless, 30 g ai/ha or less, 28 g ai/ha or less, 26 g ai/ha or less, 24 gai/ha or less, 22 g ai/ha or less, 20 g ai/ha or less, 19 g ai/ha orless, 18 g ai/ha or less, 17 g ai/ha or less, 16 g ai/ha or less, 15 gai/ha or less, 14 g ai/ha or less, 13 g ai/ha or less, 12 g ai/ha orless, 11 g ai/ha or less, 10 g ai/ha or less, 9 g ai/ha or less, 8 gai/ha or less, 7 g ai/ha or less, or 6 g ai/ha or less).

The ethoxysulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, theethoxysulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of5-120 g ai/ha (e.g., 5-110 g ai/ha, 5-100 g ai/ha, 5-90 g ai/ha, 8-120 gai/ha, 8-100 g ai/ha, 8-80 g ai/ha, 10-120 g ai/ha, 10-100 g ai/ha,10-80 g ai/ha, 15-120 g ai/ha, 15-100 g ai/ha, 15-80 g ai/ha, or 20-100g ai/ha).

Flupyrsulfuron

Compositions and methods of the present disclosure can includeflupyrsulfuron or an agriculturally acceptable salt or ester thereof.Flupyrsulfuron-methyl sodium, shown below, is a sulfonylurea that isused, e.g., for post-emergent control of grass and broadleaf weeds incereals. Flupyrsulfuron, as well as methods of preparing flupyrsulfuron,are known in the art. Its herbicidal activity is described in ThePesticide Manual, Fifteenth Edition, 2009.

In certain embodiments, the carboxylic acid or a salt thereof, or adifferent ester, e.g., alkyl or aralkyl ester, with respect to themethyl ester moiety is utilized. In certain embodiments, a differentsalt or non-ionic form is utilized.

The flupyrsulfuron or agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount sufficient to induce a herbicidal effect. Insome embodiments, the flupyrsulfuron or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 2.5 g ai/ha or more (e.g., 2.55 gai/ha or more, 2.6 g ai/ha or more, 2.65 g ai/ha or more, 2.7 g ai/ha ormore, 2.75 g ai/ha or more, 2.8 g ai/ha or more, 2.85 g ai/ha or more,2.9 g ai/ha or more, 2.95 g ai/ha or more, 3.0 g ai/ha or more, 3.05 gai/ha or more, 3.1 g ai/ha or more, 3.15 g ai/ha or more, 3.2 g ai/ha ormore, 3.25 g ai/ha or more, 3.3 g ai/ha or more, 3.35 g ai/ha or more,3.4 g ai/ha or more, 3.45 g ai/ha or more, 3.5 g ai/ha or more, 3.6 gai/ha or more, 3.7 g ai/ha or more, 3.8 g ai/ha or more, 3.9 g ai/ha ormore, 4 g ai/ha or more, 4.1 g ai/ha or more, 4.2 g ai/ha or more, 4.3 gai/ha or more, 4.4 g ai/ha or more, 4.5 g ai/ha or more, 4.6 g ai/ha ormore, 4.7 g ai/ha or more, 4.8 g ai/ha or more, 4.9 g ai/ha or more, 5 gai/ha or more, 5.1 g ai/ha or more, 5.2 g ai/ha or more, 5.3 g ai/ha ormore, 5.4 g ai/ha or more, 5.5 g ai/ha or more, 5.6 g ai/ha or more, 5.7g ai/ha or more, 5.8 g ai/ha or more, 5.9 g ai/ha or more, 6 g ai/ha ormore, 6.1 g ai/ha or more, 6.2 g ai/ha or more, 6.3 g ai/ha or more, 6.4g ai/ha or more, 6.5 g ai/ha or more, 6.6 g ai/ha or more, 6.7 g ai/haor more, 6.8 g ai/ha or more, 6.9 g ai/ha or more, 7 g ai/ha or more,7.1 g ai/ha or more, 7.2 ai/ha or more, 7.3 g ai/ha or more, 7.4 g ai/haor more, 7.5 g ai/ha or more, 7.6 g ai/ha or more, 7.7 g ai/ha or more,7.8 g ai/ha or more, 7.9 g ai/ha or more, 8 g ai/ha or more, 8.1 g ai/haor more, 8.2 g ai/ha or more, 8.3 g ai/ha or more, 8.4 ai/ha or more,8.5 g ai/ha or more, 8.6 g ai/ha or more, 8.7 g ai/ha or more, 8.8 gai/ha or more, 8.9 g ai/ha or more, 9 g ai/ha or more, 9.1 g ai/ha ormore, 9.2 g ai/ha or more, 9.3 g ai/ha or more, 9.4 g ai/ha or more, 9.5g ai/ha or more, 9.6 g ai/ha or more, 9.7 g ai/ha or more, 9.8 g ai/haor more, or 9.9 g ai/ha or more).

In some embodiments, the flupyrsulfuron or agriculturally acceptablesalt or ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 10 g ai/ha or less (e.g., 9.9 gai/ha or less, 9.8 g ai/ha or less, 9.7 g ai/ha or less, 9.6 g ai/ha orless, 9.5 g ai/ha or less, 9.4 g ai/ha or less, 9.3 g ai/ha or less, 9.2g ai/ha or less, 9.1 g ai/ha or less, 9 g ai/ha or less, 8.9 g ai/ha orless, 8.8 g ai/ha or less, 8.7 g ai/ha or less, 8.6 g ai/ha or less, 8.5g ai/ha or less, 8.4 g ai/ha or less, 8.3 g ai/ha or less, 8.2 g ai/haor less, 8.1 g ai/ha or less, 8 g ai/ha or less, 7.9 g ai/ha or less,7.8 g ai/ha or less, 7.7 g ai/ha or less, 7.6 g ai/ha or less, 7.5 gai/ha or less, 7.4 g ai/ha or less, 7.3 g ai/ha or less, 7.2 g ai/ha orless, 7.1 g ai/ha or less, 7 g ai/ha or less, 6.9 g ai/ha or less, 6.8 gai/ha or less, 6.7 g ai/ha or less, 6.6 g ai/ha or less, 6.5 g ai/ha orless, 6.4 g ai/ha or less, 6.3 g ai/ha or less, 6.2 g ai/ha or less, 6.1g ai/ha or less, 6 g ai/ha or less, 5.9 g ai/ha or less, 5.8 g ai/ha orless, 5.7 g ai/ha or less, 5.6 g ai/ha or less, 5.5 g ai/ha or less, 5.4g ai/ha or less, 5.3 g ai/ha or less, 5.2 g ai/ha or less, 5.1 g ai/haor less, 5 g ai/ha or less, 4.9 g ai/ha or less, 4.8 g ai/ha or less,4.7 g ai/ha or less, 4.6 g ai/ha or less, 4.5 g ai/ha or less, 4.4 gai/ha or less, 4.3 g ai/ha or less, 4.2 g ai/ha or less, 4.1 g ai/ha orless, 4 g ai/ha or less, 3.9 g ai/ha or less, 3.8 g ai/ha or less, 3.7 gai/ha or less, 3.6 g ai/ha or less, 3.5 g ai/ha or less, 3.45 g ai/ha orless, 3.4 g ai/ha or less, 3.35 g ai/ha or less, 3.3 g ai/ha or less,3.25 g ai/ha or less, 3.2 g ai/ha or less, 3.15 g ai/ha or less, 3.1 gai/ha or less, 3.05 g ai/ha or less, 3 g ai/ha or less, 2.95 g ai/ha orless, 2.9 g ai/ha or less, 2.85 g ai/ha or less, 2.8 g ai/ha or less,2.75 g ai/ha or less, 2.7 g ai/ha or less, 2.65 g ai/ha or less, 2.6 gai/ha or less, or 2.55 g ai/ha or less).

The flupyrsulfuron or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the flupyrsulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 2.5-10 g ai/ha (e.g., 2.5-9.5 g ai/ha, 2.5-9 g ai/ha, 2.75-10g ai/ha, 2.75-9 g ai/ha, 3-10 g ai/ha, 3.25-10 g ai/ha, 3.25-8 g ai/ha,3.5-10 g ai/ha, 3.5-9 g ai/ha, 3.5-8 g ai/ha, 3.5-7 g ai/ha, 3.5-6 gai/ha, or 3.5-5 g ai/ha).

Foramsulfuron

Compositions and methods of the present disclosure can includeforamsulfuron or an agriculturally acceptable salt thereof.Foramsulfuron, shown below, is a sulfonylurea that provides e.g.,post-emergence control of grass and broadleaf weeds in maize.Foramsulfuron, as well as methods of preparing foramsulfuron, are knownin the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, foramsulfuron can be provided as an agriculturallyacceptable salt of foramsulfuron.

The foramsulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the foramsulfuron or agriculturally acceptable salt thereof is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.5 g ai/ha or more (e.g., 3 g ai/ha or more, 3.5 g ai/ha or more, 4 gai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 5.5 g ai/ha ormore, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 gai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha ormore, 9.5 g ai/ha or more, 10 g ai/ha or more, 10.5 g ai/ha or more, 11g ai/ha or more, 11.5 g ai/ha or more, 12 g ai/ha or more, 12.5 g ai/haor more, 13 g ai/ha or more,13.5 g ai/ha or more, 14 g ai/ha or more,14.5 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/haor more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 21g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 g ai/ha ormore, 25 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha or more, 28 gai/ha or more, 29 g ai/ha or more, 30 g ai/ha or more, 31 g ai/ha ormore, 32 g ai/ha or more, 33 g ai/ha or more, 34 g ai/ha or more, 35 gai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 g ai/ha ormore, 39 g ai/ha or more, 40 g ai/ha or more, 41 g ai/ha or more, 42 gai/ha or more, 43 g ai/ha or more, 44 g ai/ha or more, 45 g ai/ha ormore, 46 g ai/ha or more, 47 g ai/ha or more, 48 g ai/ha or more, 49 gai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 g ai/ha ormore, 53 g ai/ha or more, 54 g ai/ha or more, 55 g ai/ha or more, 56 gai/ha or more, 57 g ai/ha or more, 58 g ai/ha or more, or 59 g ai/ha ormore).

In some embodiments, the foramsulfuron or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 60 g ai/ha or less (e.g., 59 g ai/ha or less,58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/haor less, 54 g ai/ha or less, 53 g ai/ha or less, 52 g ai/ha or less, 51g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha orless, 47 g ai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 gai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha orless, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 gai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha orless, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 gai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha orless, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 gai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha orless, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 gai/ha or less, 15 g ai/ha or less, 14.5 g ai/ha or less, 14 g ai/ha orless, 13.5 g ai/ha or less, 13 g ai/ha or less, 12.5 g ai/ha or less, 12g ai/ha or less, 11.5 g ai/ha or less, 11 g ai/ha or less, 10.5 g ai/haor less, 10 g ai/ha or less, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5g ai/ha or less, 8 g ai/ha or less, 7.5 g ai/ha or less, 7 g ai/ha orless, 6.5 g ai/ha or less, 6 g ai/ha or less, 5.5 g ai/ha or less, 5 gai/ha or less, 4.5 g ai/ha or less, 4 g ai/ha or less, 3.5 g ai/ha orless, or 3 g ai/ha or less).

The foramsulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, theforamsulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of2.5-60 g ai/ha (e.g., 2.5-59 g ai/ha, 2.5-58 g ai/ha, 2.5-57 g ai/ha,2.5-55 g ai/ha, 5-60 g ai/ha, 5-59 g ai/ha, 5-58 g ai/ha, 5-57 g ai/ha,5-55 g ai/ha, 7.5-60 g ai/ha, 7.5-58 g ai/ha, 7.5-55 g ai/ha, 10-60 gai/ha, 10-58 g ai/ha, 10-55 g ai/ha, 12.5-60 g ai/ha, 12.5-55 g ai/ha,or 15-55 g ai/ha).

Halosulfuron

Compositions and methods of the present disclosure can includehalosulfuron or an agriculturally acceptable salt or ester thereof.Halosulfuron-methyl, shown below, is a sulfonylurea that hasdemonstrated activity for the control of annual broadleaf weeds andnutsedge species, in maize, sugar cane, rice, sorghum, nuts, and turf.Halosulfuron, as well as methods of preparing halosulfuron, are known inthe art. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, halosulfuron can be provided as an agriculturallyacceptable salt or ester of halosulfuron.

The halosulfuron or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the halosulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 4.375 g ai/ha or more (e.g., 4.5 g ai/ha or more, 4.75 g ai/haor more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 gai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha ormore, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 gai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha ormore, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 gai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha ormore, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 gai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha ormore, 122 g ai/ha or more, 124 g ai/ha or more, 126 g ai/ha or more, 128g ai/ha or more, 130 g ai/ha or more, 131 g ai/ha or more, 132 g ai/haor more, 133 g ai/ha or more, 134 g ai/ha or more, 135 g ai/ha or more,136 g ai/ha or more, 137 g ai/ha or more, 138 g ai/ha or more, or 139 gai/ha or more).

In some embodiments, the halosulfuron or agriculturally acceptable esterthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 140 g ai/ha or less (e.g., 139 g ai/ha orless, 138 g ai/ha or less, 137 g ai/ha or less, 136 g ai/ha or less, 135g ai/ha or less, 134 g ai/ha or less, 133 g ai/ha or less, 132 g ai/haor less, 131 g ai/ha or less, 130 g ai/ha or less, 129 g ai/ha or less,128 g ai/ha or less, 126 g ai/ha or less, 124 g ai/ha or less, 122 gai/ha or less, 120 g ai/ha or less, 115 g ai/ha or less, 110 g ai/ha orless, 105 g ai/ha or less, 100 g ai/ha or less, 95 g ai/ha or less, 90 gai/ha or less, 85 g ai/ha or less, 80 g ai/ha or less, 75 g ai/ha orless, 70 g ai/ha or less, 65 g ai/ha or less, 60 g ai/ha or less, 55 gai/ha or less, 50 g ai/ha or less, 45 g ai/ha or less, 40 g ai/ha orless, 35 g ai/ha or less, 30 g ai/ha or less, 25 g ai/ha or less, 20 gai/ha or less, 15 g ai/ha or less, 10 g ai/ha or less, 9 g ai/ha orless, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/ha or less, 5 g ai/haor less, 4.75 g ai/ha or less, or 4.5 g ai/ha or less).

The halosulfuron or an agriculturally acceptable ester thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thehalosulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of4.375-140 g ai/ha (e.g., 4.375-120 g ai/ha, 4.375-100 g ai/ha, 4.5-140 gai/ha, 4.5-120 g ai/ha, 4.5-100 g ai/ha, 5-140 g ai/ha, 5-120 g ai/ha,5-100 g ai/ha, 10-140 g ai/ha, 10-120 g ai/ha, 10-100 g ai/ha, 25-140 gai/ha, or 25-100 g ai/ha).

Iodosulfuron

Compositions and methods of the present disclosure can includeiodosulfuron or an agriculturally acceptable salt or ester thereof.lodosulfuron-methyl-sodium, shown below, is a sulfonylurea thatprovides, e.g., post-emergence control of grass and broadleaf weeds inwinter, spring and durum wheat, triticale, rye and spring barley.lodosulfuron, as well as methods of preparing iodosulfuron, are known inthe art. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In certain embodiments, the carboxylic acid or a salt thereof, or adifferent ester, e.g., alkyl or aralkyl ester, with respect to themethyl ester moiety is utilized. In certain embodiments, a differentsalt or non-ionic form is utilized.

The iodosulfuron or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the iodosulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 1.25 g ai/ha or more (e.g., 1.3 g ai/ha or more, 1.4 g ai/haor more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.7 g ai/ha or more,1.8 g ai/ha or more, 1.9 g ai/ha or more, 2.0 g ai/ha or more, 2.1 gai/ha or more, 2.2 g ai/ha or more, 2.3 g ai/ha or more, 2.3 g ai/ha ormore, 2.4 g ai/ha or more, 2.5 g ai/ha or more, 2.6 g ai/ha or more, 2.7g ai/ha or more, 2.8 g ai/ha or more, 2.9 g ai/ha or more, 3.0 g ai/haor more, 3.1 g ai/ha or more, 3.2 g ai/ha or more, 3.3 g ai/ha or more,3.4 g ai/ha or more, 3.5 g ai/ha or more, 3.6 g ai/ha or more, 3.7 gai/ha or more, 3.8 g ai/ha or more, 3.9 g ai/ha or more, 4 g ai/ha ormore, 4.1 g ai/ha or more, 4.2 g ai/ha or more, 4.3 g ai/ha or more, 4.4g ai/ha or more, 4.5 g ai/ha or more, 4.6 g ai/ha or more, 4.7 g ai/haor more, 4.8 g ai/ha or more, 4.9 g ai/ha or more, 5 g ai/ha or more,5.1 g ai/ha or more, 5.2 g ai/ha or more, 5.3 g ai/ha or more, 5.4 gai/ha or more, 5.5 g ai/ha or more, 5.6 g ai/ha or more, 5.7 g ai/ha ormore, 5.8 g ai/ha or more, 5.9 g ai/ha or more, 6 g ai/ha or more, 6.1 gai/ha or more, 6.2 g ai/ha or more, 6.3 g ai/ha or more, 6.4 g ai/ha ormore, 6.5 g ai/ha or more, 6.6 g ai/ha or more, 6.7 g ai/ha or more, 6.8g ai/ha or more, 6.9 g ai/ha or more, 7 g ai/ha or more, 7.1 g ai/ha ormore, 7.2 ai/ha or more, 7.3 g ai/ha or more, 7.4 g ai/ha or more, 7.5 gai/ha or more, 7.6 g ai/ha or more, 7.7 g ai/ha or more, 7.8 g ai/ha ormore, 7.9 g ai/ha or more, 8 g ai/ha or more, 8.1 g ai/ha or more, 8.2 gai/ha or more, 8.3 g ai/ha or more, 8.4 ai/ha or more, 8.5 g ai/ha ormore, 8.6 g ai/ha or more, 8.7 g ai/ha or more, 8.8 g ai/ha or more, 8.9g ai/ha or more, 9 g ai/ha or more, 9.1 g ai/ha or more, 9.2 g ai/ha ormore, 9.3 g ai/ha or more, 9.4 g ai/ha or more, 9.5 g ai/ha or more, 9.6g ai/ha or more, 9.7 g ai/ha or more, 9.8 g ai/ha or more, or 9.9 gai/ha or more).

In some embodiments, the iodosulfuron or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 10 g ai/ha or less (e.g., 9.9 gai/ha or less, 9.8 g ai/ha or less, 9.7 g ai/ha or less, 9.6 g ai/ha orless, 9.5 g ai/ha or less, 9.4 g ai/ha or less, 9.3 g ai/ha or less, 9.2g ai/ha or less, 9.1 g ai/ha or less, 9 g ai/ha or less, 8.9 g ai/ha orless, 8.8 g ai/ha or less, 8.7 g ai/ha or less, 8.6 g ai/ha or less, 8.5g ai/ha or less, 8.4 g ai/ha or less, 8.3 g ai/ha or less, 8.2 g ai/haor less, 8.1 g ai/ha or less, 8 g ai/ha or less, 7.9 g ai/ha or less,7.8 g ai/ha or less, 7.7 g ai/ha or less, 7.6 g ai/ha or less, 7.5 gai/ha or less, 7.4 g ai/ha or less, 7.3 g ai/ha or less, 7.2 g ai/ha orless, 7.1 g ai/ha or less, 7 g ai/ha or less, 6.9 g ai/ha or less, 6.8 gai/ha or less, 6.7 g ai/ha or less, 6.6 g ai/ha or less, 6.5 g ai/ha orless, 6.4 g ai/ha or less, 6.3 g ai/ha or less, 6.2 g ai/ha or less, 6.1g ai/ha or less, 6 g ai/ha or less, 5.9 g ai/ha or less, 5.8 g ai/ha orless, 5.7 g ai/ha or less, 5.6 g ai/ha or less, 5.5 g ai/ha or less, 5.4g ai/ha or less, 5.3 g ai/ha or less, 5.2 g ai/ha or less, 5.1 g ai/haor less, 5 g ai/ha or less, 4.9 g ai/ha or less, 4.8 g ai/ha or less,4.7 g ai/ha or less, 4.6 g ai/ha or less, 4.5 g ai/ha or less, 4.4 gai/ha or less, 4.3 g ai/ha or less, 4.2 g ai/ha or less, 4.1 g ai/ha orless, 4 g ai/ha or less, 3.9 g ai/ha or less, 3.8 g ai/ha or less, 3.7 gai/ha or less, 3.6 g ai/ha or less, 3.5 g ai/ha or less, 3.4 g ai/ha orless, 3.3 g ai/ha or less, 3.2 g ai/ha or less, 3.1 g ai/ha or less, 3 gai/ha or less, 2.9 g ai/ha or less, 2.8 g ai/ha or less, 2.7 g ai/ha orless, 2.6 g ai/ha or less, 2.5 g ai/ha or less, 2.4 g ai/ha or less, 2.3g ai/ha or less, 2.2 g ai/ha or less, 2.1 g ai/ha or less, 2.0 g ai/haor less, 1.9 g ai/ha or less, 1.8 g ai/ha or less, 1.7 g ai/ha or less,1.6 g ai/ha or less, 1.5 g ai/ha or less, 1.4 g ai/ha or less, or 1.3 gai/ha or less).

The iodosulfuron or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the iodosulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 1.25-10 g ai/ha (e.g., 1.25-9 g ai/ha, 1.25-8 g ai/ha,1.25-7.5 g ai/ha, 1.5-10 g ai/ha, 1.5-9 g ai/ha, 1.5-8 g ai/ha, 1.5-7.5g ai/ha, 2-10 g ai/ha, 2-9 g ai/ha, 2-8 g ai/ha, 2-7.5 g ai/ha, 2.5-10 gai/ha, or 2.5-9 g ai/ha).

Mesosulfuron

Compositions and methods of the present disclosure can includemesosulfuron or an agriculturally acceptable salt or ester thereof.Mesosulfuron-methyl, shown below, is a sulfonylurea that provides, e.g.,early to mid post-emergence control of grass and some broadleaf weeds inwinter, spring, and durum wheat, triticale, and rye. Mesosulfuron, aswell as methods of preparing mesosulfuron, are known in the art. Itsherbicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009.

In certain embodiments, the carboxylic acid or a salt thereof, or adifferent ester, e.g., alkyl or aralkyl ester, with respect to themethyl ester moiety is utilized.

The mesosulfuron or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the mesosulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 1.5 g ai/ha or more (e.g., 1.55 g ai/ha or more, 1.6 g ai/haor more, 1.65 g ai/ha or more, 1.7 g ai/ha or more, 1.75 g ai/ha ormore, 1.8 g ai/ha or more, 1.85 g ai/ha or more, 1.9 g ai/ha or more,1.95 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 gai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha ormore, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha ormore, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/haor more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha ormore, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 gai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha ormore, 24 g ai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 gai/ha or more, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha ormore, 31 g ai/ha or more, 32 g ai/ha or more, 33 g ai/ha or more, 34 gai/ha or more, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha ormore, 38 g ai/ha or more, 39 g ai/ha or more, 40 g ai/ha or more, 41 gai/ha or more, 42 g ai/ha or more, 43 g ai/ha or more, or 44 g ai/ha ormore).

In some embodiments, the mesosulfuron or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 45 g ai/ha or less (e.g., 44 gai/ha or less, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha orless, 40 g ai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 gai/ha or less, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha orless, 33 g ai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 gai/ha or less, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha orless, 26 g ai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 gai/ha or less, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha orless, 19 g ai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 gai/ha or less, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha orless, 12 g ai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, 9 gai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/ha or less,5 g ai/ha or less, 4.75 g ai/ha or less, 4.5 g ai/ha or less, 4.25 gai/ha or less, 4 g ai/ha or less, 3.75 g ai/ha or less, 3.5 g ai/ha orless, 3.25 g ai/ha or less, 3 g ai/ha or less, 2.75 g ai/ha or less, 2.5g ai/ha or less, 2.25 g ai/ha or less, 2 g ai/ha or less, 1.95 g ai/haor less, 1.9 g ai/ha or less, 1.85 g ai/ha or less, 1.8 g ai/ha or less,1.75 g ai/ha or less, 1.7 g ai/ha or less, 1.65 g ai/ha or less, 1.6 gai/ha or less, or 1.55 g ai/ha or less).

The mesosulfuron or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the mesosulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 1.5-45 g ai/ha (e.g., 1.5-42 g ai/ha, 1.5-40 g ai/ha, 1.75-45g ai/ha, 1.75-40 g ai/ha, 2-45 g ai/ha, 2.25-45 g ai/ha, 2.25-40 gai/ha, 2.5-45 g ai/ha, 2.5-40 g ai/ha, 2.5-35 g ai/ha, 2.75-45 g ai/ha,2.75-40 g ai/ha, or 4-40 g ai/ha).

Metsulfuron

Compositions and methods of the present disclosure can includemetsulfuron or an agriculturally acceptable salt or ester thereof.Metsulfuron-methyl, shown below, is a sulfonylurea that controls, e.g.,grass and broadleaf weeds in wheat, barley, rice, oats, and triticale.Metsulfuron, as well as methods of preparing metsulfuron, are known inthe art. Its herbicidal activity is described in The Pesticide Manual,Fifteenth Edition, 2009.

In certain embodiments, the carboxylic acid or a salt thereof, or adifferent ester, e.g., alkyl or aralkyl ester, with respect to themethyl ester moiety is utilized.

The metsulfuron or agriculturally acceptable salt or ester thereof canbe applied to vegetation or an area adjacent the vegetation or appliedto soil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the metsulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of 1g ai/ha or more (e.g., 1.25 g ai/ha or more, 1.3 g ai/ha or more, 1.4 gai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.7 g ai/ha ormore, 1.8 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.1 gai/ha or more, 2.2 g ai/ha or more, 2.3 g ai/ha or more, 2.3 g ai/ha ormore, 2.4 g ai/ha or more, 2.5 g ai/ha or more, 2.6 g ai/ha or more, 2.7g ai/ha or more, 2.8 g ai/ha or more, 2.9 g ai/ha or more, 3 g ai/ha ormore, 3.1 g ai/ha or more, 3.2 g ai/ha or more, 3.3 g ai/ha or more, 3.4g ai/ha or more, 3.5 g ai/ha or more, 3.6 g ai/ha or more, 3.7 g ai/haor more, 3.8 g ai/ha or more, 3.9 g ai/ha or more, 4 g ai/ha or more,4.1 g ai/ha or more, 4.2 g ai/ha or more, 4.3 g ai/ha or more, 4.4 gai/ha or more, 4.5 g ai/ha or more, 4.6 g ai/ha or more, 4.7 g ai/ha ormore, 4.8 g ai/ha or more, 4.9 g ai/ha or more, 5 g ai/ha or more, 5.1 gai/ha or more, 5.2 g ai/ha or more, 5.3 g ai/ha or more, 5.4 g ai/ha ormore, 5.5 g ai/ha or more, 5.6 g ai/ha or more, 5.7 g ai/ha or more, 5.8g ai/ha or more, 5.9 g ai/ha or more, 6 g ai/ha or more, 6.1 g ai/ha ormore, 6.2 g ai/ha or more, 6.3 g ai/ha or more, 6.4 g ai/ha or more, 6.5g ai/ha or more, 6.6 g ai/ha or more, 6.7 g ai/ha or more, 6.8 g ai/haor more, 6.9 g ai/ha or more, 7 g ai/ha or more, 7.1 g ai/ha or more,7.2 ai/ha or more, 7.3 g ai/ha or more, 7.4 g ai/ha or more, 7.5 g ai/haor more, 7.6 g ai/ha or more, 7.7 g ai/ha or more, 7.8 g ai/ha or more,7.9 g ai/ha or more, 8 g ai/ha or more, 8.1 g ai/ha or more, 8.2 g ai/haor more, 8.3 g ai/ha or more, 8.4 ai/ha or more, 8.5 g ai/ha or more,8.6 g ai/ha or more, 8.7 g ai/ha or more, 8.8 g ai/ha or more, 8.9 gai/ha or more, 9 g ai/ha or more, 9.1 g ai/ha or more, 9.2 g ai/ha ormore, 9.3 g ai/ha or more, 9.4 g ai/ha or more, 9.5 g ai/ha or more, 9.6g ai/ha or more, 9.7 g ai/ha or more, 9.8 g ai/ha or more, 9.9 g ai/haor more, 10 g ai/ha or more, 10.1 g ai/ha or more, 10.2 g ai/ha or more,10.3 g ai/ha or more, 10.4 g ai/ha or more, 10.5 g ai/ha or more, 10.6 gai/ha or more, 10.7 g ai/ha or more, 10.8 g ai/ha or more, 10.9 g ai/haor more, 11 g ai/ha or more, 11.1 g ai/ha or more, 11.2 g ai/ha or more,11.3 g ai/ha or more, 11.4 g ai/ha or more, 11.5 g ai/ha or more, 11.6 gai/ha or more, 11.7 g ai/ha or more, 11.8 g ai/ha or more, or 11.9 gai/ha or more).

In some embodiments, the metsulfuron or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 12 g ai/ha or less (e.g., 11.9 gai/ha or less, 11.8 g ai/ha or less, 11.7 g ai/ha or less, 11.6 g ai/haor less, 11.5 g ai/ha or less, 11.4 g ai/ha or less, 11.3 g ai/ha orless, 11.2 g ai/ha or less, 11.1 g ai/ha or less, 11 g ai/ha or less,10.9 g ai/ha or less, 10.8 g ai/ha or less, 10.7 g ai/ha or less, 10.6 gai/ha or less, 10.5 g ai/ha or less, 10.4 g ai/ha or less, 10.3 g ai/haor less, 10.2 g ai/ha or less, 10.1 g ai/ha or less, 10 g ai/ha or less,9.9 g ai/ha or less, 9.8 g ai/ha or less, 9.7 g ai/ha or less, 9.6 gai/ha or less, 9.5 g ai/ha or less, 9.4 g ai/ha or less, 9.3 g ai/ha orless, 9.2 g ai/ha or less, 9.1 g ai/ha or less, 9 g ai/ha or less, 8.9 gai/ha or less, 8.8 g ai/ha or less, 8.7 g ai/ha or less, 8.6 g ai/ha orless, 8.5 g ai/ha or less, 8.4 g ai/ha or less, 8.3 g ai/ha or less, 8.2g ai/ha or less, 8.1 g ai/ha or less, 8 g ai/ha or less, 7.9 g ai/ha orless, 7.8 g ai/ha or less, 7.7 g ai/ha or less, 7.6 g ai/ha or less, 7.5g ai/ha or less, 7.4 g ai/ha or less, 7.3 g ai/ha or less, 7.2 g ai/haor less, 7.1 g ai/ha or less, 7 g ai/ha or less, 6.9 g ai/ha or less,6.8 g ai/ha or less, 6.7 g ai/ha or less, 6.6 g ai/ha or less, 6.5 gai/ha or less, 6.4 g ai/ha or less, 6.3 g ai/ha or less, 6.2 g ai/ha orless, 6.1 g ai/ha or less, 6 g ai/ha or less, 5.9 g ai/ha or less, 5.8 gai/ha or less, 5.7 g ai/ha or less, 5.6 g ai/ha or less, 5.5 g ai/ha orless, 5.4 g ai/ha or less, 5.3 g ai/ha or less, 5.2 g ai/ha or less, 5.1g ai/ha or less, 5 g ai/ha or less, 4.9 g ai/ha or less, 4.8 g ai/ha orless, 4.7 g ai/ha or less, 4.6 g ai/ha or less, 4.5 g ai/ha or less, 4.4g ai/ha or less, 4.3 g ai/ha or less, 4.2 g ai/ha or less, 4.1 g ai/haor less, 4 g ai/ha or less, 3.9 g ai/ha or less, 3.8 g ai/ha or less,3.7 g ai/ha or less, 3.6 g ai/ha or less, 3.5 g ai/ha or less, 3.4 gai/ha or less, 3.3 g ai/ha or less, 3.2 g ai/ha or less, 3.1 g ai/ha orless, 3 g ai/ha or less, 2.9 g ai/ha or less, 2.8 g ai/ha or less, 2.7 gai/ha or less, 2.6 g ai/ha or less, 2.5 g ai/ha or less, 2.4 g ai/ha orless, 2.3 g ai/ha or less, 2.2 g ai/ha or less, 2.1 g ai/ha or less, 2 gai/ha or less, 1.9 g ai/ha or less, 1.8 g ai/ha, 1.7 g ai/ha or less,1.6 g ai/ha or less, 1.5 g ai/ha or less, 1.4 g ai/ha or less, 1.3 gai/ha or less, or 1.25 g ai/ha or less).

The metsulfuron or an agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the metsulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 1-12 g ai/ha (e.g., 1-11 g ai/ha, 1-10 g ai/ha, 1-8 g ai/ha,1.25-12 g ai/ha, 1.25-10 g ai/ha, 1.25-8 g ai/ha, 1.5-12 g ai/ha, 1.5-10g ai/ha, 2-12 g ai/ha, 2-10 g ai/ha, 2-8 g ai/ha, 2-7.5 g ai/ha, 2.5-12g ai/ha, or 2.5-10 g ai/ha).

Nicosulfuron

Compositions and methods of the present disclosure can includenicosulfuron or an agriculturally acceptable salt thereof. Nicosulfuron,shown below, is a sulfonylurea that provides, e.g., selectivepost-emergence control in maize of annual grass weeds, includingSetaria, Echinochloa, Digitaria, Panicum, Lolium and Avena spp.,broadleaf weeds, including Amaranthus spp. and Cruciferae, andperennials such as Sorghum halepense and Agropyron repens. Nicosulfuron,as well as methods of preparing nicosulfuron, are known in the art. Itsherbicidal activity is described in The Pesticide Manual, FifteenthEdition, 2009.

In some embodiments, nicosulfuron can be provided as an agriculturallyacceptable salt of nicosulfuron.

The nicosulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the nicosulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of8.75 g ai/ha or more (e.g., 9 g ai/ha or more, 10 g ai/ha or more, 11 gai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha ormore, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 gai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 21 g ai/ha ormore, 22 g ai/ha or more, 23 g ai/ha or more, 24 g ai/ha or more, 25 gai/ha or more, 26 g ai/ha or more, 27 g ai/ha or more, 28 g ai/ha ormore, 29 g ai/ha or more, 30 g ai/ha or more, 31 g ai/ha or more, 32 gai/ha or more, 33 g ai/ha or more, 34 g ai/ha or more, 35 g ai/ha ormore, 36 g ai/ha or more, 37 g ai/ha or more, 38 g ai/ha or more, 39 gai/ha or more, 40 g ai/ha or more, 41 g ai/ha or more, 42 g ai/ha ormore, 43 g ai/ha or more, 44 g ai/ha or more, 45 g ai/ha or more, 46 gai/ha or more, 47 g ai/ha or more, 48 g ai/ha or more, 49 g ai/ha ormore, 50 g ai/ha or more, 51 g ai/ha or more, 52 g ai/ha or more, 53 gai/ha or more, 54 g ai/ha or more, 55 g ai/ha or more, 56 g ai/ha ormore, 57 g ai/ha or more, 58 g ai/ha or more, 59 g ai/ha or more, 60 gai/ha or more, 61 g ai/ha or more, 62 g ai/ha or more, 63 g ai/ha ormore, 64 g ai/ha or more, 65 g ai/ha or more, 66 g ai/ha or more, 67 gai/ha or more, 68 g ai/ha or more, or 69 g ai/ha or more).

In some embodiments, the nicosulfuron or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 70 g ai/ha or less (e.g., 69 g ai/ha or less,68 g ai/ha or less, 67 g ai/ha or less, 66 g ai/ha or less, 65 g ai/haor less, 64 g ai/ha or less, 63 g ai/ha or less, 62 g ai/ha or less, 61g ai/ha or less, 60 g ai/ha or less, 59 g ai/ha or less, 58 g ai/ha orless, 57 g ai/ha or less, 56 g ai/ha or less, 55 g ai/ha or less, 54 gai/ha or less, 53 g ai/ha or less, 52 g ai/ha or less, 51 g ai/ha orless, 50 g ai/ha or less, 49 g ai/ha or less, 48 g ai/ha or less, 47 gai/ha or less, 46 g ai/ha or less, 45 g ai/ha or less, 44 g ai/ha orless, 43 g ai/ha or less, 42 g ai/ha or less, 41 g ai/ha or less, 40 gai/ha or less, 39 g ai/ha or less, 38 g ai/ha or less, 37 g ai/ha orless, 36 g ai/ha or less, 35 g ai/ha or less, 34 g ai/ha or less, 33 gai/ha or less, 32 g ai/ha or less, 31 g ai/ha or less, 30 g ai/ha orless, 29 g ai/ha or less, 28 g ai/ha or less, 27 g ai/ha or less, 26 gai/ha or less, 25 g ai/ha or less, 24 g ai/ha or less, 23 g ai/ha orless, 22 g ai/ha or less, 21 g ai/ha or less, 20 g ai/ha or less, 19 gai/ha or less, 18 g ai/ha or less, 17 g ai/ha or less, 16 g ai/ha orless, 15 g ai/ha or less, 14 g ai/ha or less, 13 g ai/ha or less, 12 gai/ha or less, 11 g ai/ha or less, 10 g ai/ha or less, or 9 g ai/ha orless).

The nicosulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thenicosulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of8.75-70 g ai/ha (e.g., 8.75-68 g ai/ha, 8.75-65 g ai/ha, 9-60 g ai/ha,10-70 g ai/ha, 10-68 g ai/ha, 10-65 g ai/ha, 10-60 g ai/ha, 11-70 gai/ha, 11-68 g ai/ha, 11-65 g ai/ha, 11-60 g ai/ha, 20-60 g ai/ha, or20-50 g ai/ha).

Orthosulfamuron

Compositions and methods of the present disclosure can includeorthosulfamuron or an agriculturally acceptable salt thereof.Orthosulfamuron, shown below, is a sulfonylurea that provides, e.g.,early post-emergence control of annual and perennial broadleaf weeds andsedges in rice, cereals, pastures, and sugar cane. Orthosulfamuron, aswell as methods of preparing orthosulfamuron, are known in the art. Itsherbicidal activity is described, for example, in The Pesticide Manual,Fifteenth Edition, 2009.

In some embodiments, orthosulfamuron can be provided as anagriculturally acceptable salt of orthosulfamuron.

The orthosulfamuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the orthosulfamuron or agriculturally acceptable salt thereof is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of7.5 g ai/ha or more (e.g., 7.75 g ai/ha or more, 8 g ai/ha or more, 8.25g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha ormore, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 gai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha ormore, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 gai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha ormore, 24 g ai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 27 gai/ha or more, 28 g ai/ha or more, 29 g ai/ha or more, 30 g ai/ha ormore, 31 g ai/ha or more, 32 g ai/ha or more, 33 g ai/ha or more, 34 gai/ha or more, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha ormore, 38 g ai/ha or more, 39 g ai/ha or more, 40 g ai/ha or more, 41 gai/ha or more, 42 g ai/ha or more, 43 g ai/ha or more, 44 g ai/ha ormore, 45 g ai/ha or more, 46 g ai/ha or more, 47 g ai/ha or more, 48 gai/ha or more, 49 g ai/ha or more, 50 g ai/ha or more, 51 g ai/ha ormore, 52 g ai/ha or more, 53 g ai/ha or more, 54 g ai/ha or more, 55 gai/ha or more, 56 g ai/ha or more, 57 g ai/ha or more, 58 g ai/ha ormore, 59 g ai/ha or more, 60 g ai/ha or more, 61 g ai/ha or more, 62 gai/ha or more, 63 g ai/ha or more, 64 g ai/ha or more, 65 g ai/ha ormore, 66 g ai/ha or more, 67 g ai/ha or more, 68 g ai/ha or more, 69 gai/ha or more, 70 g ai/ha or more, 71 g ai/ha or more, 72 g ai/ha ormore, 73 g ai/ha or more, or 74 g ai/ha or more).

In some embodiments, the orthosulfamuron or agriculturally acceptablesalt thereof is applied to vegetation or an area adjacent the vegetationor applied to soil or water to prevent the emergence or growth ofvegetation in an amount of 75 g ai/ha or less (e.g., 74 g ai/ha or less,73 g ai/ha or less, 72 g ai/ha or less, 71 g ai/ha or less, 70 g ai/haor less, 69 g ai/ha or less, 68 g ai/ha or less, 67 g ai/ha or less, 66g ai/ha or less, 65 g ai/ha or less, 64 g ai/ha or less, 63 g ai/ha orless, 62 g ai/ha or less, 61 g ai/ha or less, 60 g ai/ha or less, 59 gai/ha or less, 58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha orless, 55 g ai/ha or less, 54 g ai/ha or less, 53 g ai/ha or less, 52 gai/ha or less, 51 g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha orless, 48 g ai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 gai/ha or less, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha orless, 41 g ai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 gai/ha or less, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha orless, 34 g ai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 gai/ha or less, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha orless, 27 g ai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 gai/ha or less, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha orless, 20 g ai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 gai/ha or less, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha orless, 13 g ai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 gai/ha or less, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5 g ai/ha orless, 8.25 g ai/ha or less, 8 g ai/ha or less, or 7.75 g ai/ha or less).

The orthosulfamuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, theorthosulfamuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of7.5-75 g ai/ha (e.g., 7.5-72 g ai/ha, 7.5-70 g ai/ha, 7.75-65 g ai/ha,9-75 g ai/ha, 9-72 g ai/ha, 9-70 g ai/ha, 9-65 g ai/ha, 10-75 g ai/ha,10-72 g ai/ha, 10-65 g ai/ha, 10-60 g ai/ha, 20-70 g ai/ha, or 20-50 gai/ha).

Sulfosulfuron

Compositions and methods of the present disclosure can includesulfosulfuron or an agriculturally acceptable salt thereof.Sulfosulfuron, shown below, is a sulfonylurea that provides, e.g.,control of annual broadleaf weeds and grass weeds in cereals.Sulfosulfuron, as well as methods of preparing sulfosulfuron, are knownin the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In some embodiments, sulfosulfuron can be provided as an agriculturallyacceptable salt of sulfosulfuron.

The sulfosulfuron or agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the sulfosulfuron or agriculturally acceptable salt thereof is appliedto vegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of4.375 g ai/ha or more (e.g., 4.5 g ai/ha or more, 4.75 g ai/ha or more,5 g ai/ha or more, 5.5 g ai/ha or more, 6 g ai/ha or more, 6.5 g ai/haor more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 9 gai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha ormore, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 gai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha ormore, 20 g ai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 gai/ha or more, 24 g ai/ha or more, 25 g ai/ha or more, 26 g ai/ha ormore, 27 g ai/ha or more, 28 g ai/ha or more, 29 g ai/ha or more, 30 gai/ha or more, 31 g ai/ha or more, 32 g ai/ha or more, 33 g ai/ha ormore, 34 g ai/ha or more, 35 g ai/ha or more, 36 g ai/ha or more, 37 gai/ha or more, 38 g ai/ha or more, 39 g ai/ha or more, 40 g ai/ha ormore, 41 g ai/ha or more, 42 g ai/ha or more, 43 g ai/ha or more, 44 gai/ha or more, 45 g ai/ha or more, 46 g ai/ha or more, 47 g ai/ha ormore, 48 g ai/ha or more, 49 g ai/ha or more, 50 g ai/ha or more, 51 gai/ha or more, 52 g ai/ha or more, 53 g ai/ha or more, 54 g ai/ha ormore, 55 g ai/ha or more, 56 g ai/ha or more, 57 g ai/ha or more, 58 gai/ha or more, 59 g ai/ha or more, 60 g ai/ha or more, 61 g ai/ha ormore, 62 g ai/ha or more, 63 g ai/ha or more, 64 g ai/ha or more, 65 gai/ha or more, 66 g ai/ha or more, 67 g ai/ha or more, 68 g ai/ha ormore, 69 g ai/ha or more, 70 g ai/ha or more, 71 g ai/ha or more, 72 gai/ha or more, 73 g ai/ha or more, or 74 g ai/ha or more).

In some embodiments, the sulfosulfuron or agriculturally acceptable saltthereof is applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount of 75 g ai/ha or less (e.g., 74 g ai/ha or less,73 g ai/ha or less, 72 g ai/ha or less, 71 g ai/ha or less, 70 g ai/haor less, 69 g ai/ha or less, 68 g ai/ha or less, 67 g ai/ha or less, 66g ai/ha or less, 65 g ai/ha or less, 64 g ai/ha or less, 63 g ai/ha orless, 62 g ai/ha or less, 61 g ai/ha or less, 60 g ai/ha or less, 59 gai/ha or less, 58 g ai/ha or less, 57 g ai/ha or less, 56 g ai/ha orless, 55 g ai/ha or less, 54 g ai/ha or less, 53 g ai/ha or less, 52 gai/ha or less, 51 g ai/ha or less, 50 g ai/ha or less, 49 g ai/ha orless, 48 g ai/ha or less, 47 g ai/ha or less, 46 g ai/ha or less, 45 gai/ha or less, 44 g ai/ha or less, 43 g ai/ha or less, 42 g ai/ha orless, 41 g ai/ha or less, 40 g ai/ha or less, 39 g ai/ha or less, 38 gai/ha or less, 37 g ai/ha or less, 36 g ai/ha or less, 35 g ai/ha orless, 34 g ai/ha or less, 33 g ai/ha or less, 32 g ai/ha or less, 31 gai/ha or less, 30 g ai/ha or less, 29 g ai/ha or less, 28 g ai/ha orless, 27 g ai/ha or less, 26 g ai/ha or less, 25 g ai/ha or less, 24 gai/ha or less, 23 g ai/ha or less, 22 g ai/ha or less, 21 g ai/ha orless, 20 g ai/ha or less, 19 g ai/ha or less, 18 g ai/ha or less, 17 gai/ha or less, 16 g ai/ha or less, 15 g ai/ha or less, 14 g ai/ha orless, 13 g ai/ha or less, 12 g ai/ha or less, 11 g ai/ha or less, 10 gai/ha or less, 9 g ai/ha or less, 8 g ai/ha or less, 7.5 g ai/ha orless, 7 g ai/ha or less, 6.5 g ai/ha or less, 6 g ai/ha or less, 5.5 gai/ha or less, 5 g ai/ha or less, 4.75 g ai/ha or less, or 4.5 g ai/haor less).

The sulfosulfuron or an agriculturally acceptable salt thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, thesulfosulfuron or agriculturally acceptable salt thereof is applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation in an amount of4.375-75 g ai/ha (e.g., 4.375-70 g ai/ha, 4.375-60 g ai/ha, 4.5-75 gai/ha, 4.5-70 g ai/ha, 4.5-60 g ai/ha, 5-75 g ai/ha, 5-70 g ai/ha, 5-60g ai/ha, 10-75 g ai/ha, 10-70 g ai/ha, 10-60 g ai/ha, 25-75 g ai/ha, or25-70 g ai/ha).

Thifensulfuron

Compositions and methods of the present disclosure can includethifensulfuron or an agriculturally acceptable salt or ester thereof.Thifensulfuron-methyl, shown below, is a sulfonylurea that provides,e.g., control of annual weeds in cereals, maize, and pasture.Thifensulfuron, as well as methods of preparing thifensulfuron, areknown in the art. Its herbicidal activity is described in The PesticideManual, Fifteenth Edition, 2009.

In certain embodiments, the carboxylic acid or a salt thereof, or adifferent ester, e.g., alkyl or aralkyl ester, with respect to themethyl ester moiety is utilized.

The thifensulfuron or agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount sufficient to induce a herbicidal effect. Insome embodiments, the thifensulfuron or agriculturally acceptable saltor ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 4.4 g ai/ha or more (e.g., 4.5 gai/ha or more, 4.6 g ai/ha or more, 4.7 g ai/ha or more, 4.8 g ai/ha ormore, 4.9 g ai/ha or more, 5 g ai/ha or more, 5.1 g ai/ha or more, 5.2 gai/ha or more, 5.3 g ai/ha or more, 5.4 g ai/ha or more, 5.5 g ai/ha ormore, 5.6 g ai/ha or more, 5.7 g ai/ha or more, 5.8 g ai/ha or more, 5.9g ai/ha or more, 6 g ai/ha or more, 6.1 g ai/ha or more, 6.2 g ai/ha ormore, 6.3 g ai/ha or more, 6.4 g ai/ha or more, 6.5 g ai/ha or more, 6.6g ai/ha or more, 6.7 g ai/ha or more, 6.8 g ai/ha or more, 6.9 g ai/haor more, 7 g ai/ha or more, 7.1 g ai/ha or more, 7.2 g ai/ha or more,7.3 g ai/ha or more, 7.4 g ai/ha or more, 7.5 g ai/ha or more, 7.6 gai/ha or more, 7.7 g ai/ha or more, 7.8 g ai/ha or more, 7.9 g ai/ha ormore, 8 g ai/ha or more, 8.2 g ai/ha or more, 8.4 g ai/ha or more, 8.6 gai/ha or more, 8.8 g ai/ha or more, 9 g ai/ha or more, 9.2 g ai/ha ormore, 9.4 g ai/ha or more, 9.6 g ai/ha or more, 9.8 g ai/ha or more, 10g ai/ha or more, 10.5 g ai/ha or more, 11 g ai/ha or more, 11.5 g ai/haor more, 12 g ai/ha or more, 12.5 g ai/ha or more, 13 g ai/ha or more,13.5 g ai/ha or more, 14 g ai/ha or more, 14.5 g ai/ha or more, 15 gai/ha or more, 15.5 g ai/ha or more, 16 g ai/ha or more, 16.2 g ai/ha ormore, 16.4 g ai/ha or more, 16.6 g ai/ha or more, 16.8 g ai/ha or more,17 g ai/ha or more, 17.1 g ai/ha or more, 17.2 g ai/ha or more, 17.3 gai/ha or more, or 17.4 g ai/ha or more).

In some embodiments, the thifensulfuron or agriculturally acceptablesalt or ester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 17.5 g ai/ha or less (e.g., 17.4 gai/ha or less, 17.3 g ai/ha or less, 17.2 g ai/ha or less, 17.1 g ai/haor less, 17 g ai/ha or less, 16.8 g ai/ha or less, 16.6 g ai/ha or less,16.4 g ai/ha or less, 16.2 g ai/ha or less, 16 g ai/ha or less, 15.5 gai/ha or less, 15 g ai/ha or less, 14.5 g ai/ha or less, 14 g ai/ha orless, 13.5 g ai/ha or less, 13 g ai/ha or less, 12.5 g ai/ha or less, 12g ai/ha or less, 11.5 g ai/ha or less, 11 g ai/ha or less, 10.5 g ai/haor less, 10 g ai/ha or less, 9.8 g ai/ha or less, 9.6 g ai/ha or less,9.4 g ai/ha or less, 9.2 g ai/ha or less, 9 g ai/ha or less, 8.8 g ai/haor less, 8.6 g ai/ha or less, 8.4 g ai/ha or less, 8.2 g ai/ha or less,8 g ai/ha or less, 7.9 g ai/ha or less, 7.8 g ai/ha or less, 7.7 g ai/haor less, 7.6 g ai/ha or less, 75 g ai/ha or less, 7.4 g ai/ha or less,7.3 g ai/ha or less, 7.2 g ai/ha or less, 7.1 g ai/ha or less, 7 g ai/haor less, 6.9 g ai/ha or less, 6.8 g ai/ha or less, 6.7 g ai/ha or less,6.6 g ai/ha or less, 6.5 g ai/ha or less, 6.4 g ai/ha or less, 6.3 gai/ha or less, 6.2 g ai/ha or less, 6.1 g ai/ha or less, 6 g ai/ha orless, 5.9 g ai/ha or less, 5.8 g ai/ha or less, 5.7 g ai/ha or less, 5.6g ai/ha or less, 5.5 g ai/ha or less, 5.4 g ai/ha or less, 5.3 g ai/haor less, 5.2 g ai/ha or less, 5.1 g ai/ha or less, 5 g ai/ha or less,4.9 g ai/ha or less, 4.8 g ai/ha or less, 4.7 g ai/ha or less, 4.6 gai/ha or less, or 4.5 g ai/ha or less).

The thifensulfuron or agriculturally acceptable salt or ester thereofcan be applied to vegetation or an area adjacent the vegetation orapplied to soil or water to prevent the emergence or growth ofvegetation in an amount ranging from any of the minimum values describedabove to any of the maximum values described above. In some embodiments,the thifensulfuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 4.4-17.5 g ai/ha (e.g., 4.4-16 g ai/ha, 4.4-15 g ai/ha,4.8-17.5 g ai/ha, 4.8-17.5 g ai/ha, 5-17.5 g ai/ha, 5-16 g ai/ha, 5-15 gai/ha, 6-17.5 g ai/ha, 6-16 g ai/ha, 6-15 g ai/ha, 7.5-17.5 g ai/ha,7.5-16 g ai/ha, or 7.5-15 g ai/ha).

Tribenuron

Compositions and methods of the present disclosure can includetribenuron or an agriculturally acceptable salt thereof.Tribenuron-methyl, shown below, is a sulfonylurea that provides e.g.,post-emergence control of broadleaf weeds in cereal crops, includingwheat, barley, oats, rye and triticale. Tribenuron, as well as methodsof preparing tribenuron, are known in the art. Its herbicidal activityis described in The Pesticide Manual, Fifteenth Edition, 2009.

In some embodiments, tribenuron can be provided as an agriculturallyacceptable salt or ester of tribenuron.

The tribenuron or agriculturally acceptable salt or ester thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount sufficient to induce a herbicidal effect. In some embodiments,the tribenuron or agriculturally acceptable salt or ester thereof isapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount of 3.75 g ai/ha or more (e.g., 4 g ai/ha or more, 4.25 g ai/ha ormore, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha ormore, 6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 gai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha ormore, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 gai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha ormore, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 gai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha ormore, 24 g ai/ha or more, 25 g ai/ha or more, 25.5 g ai/ha or more, 26 gai/ha or more, 26.5 g ai/ha or more, 27 g ai/ha or more, 27.5 g ai/ha ormore, 28 g ai/ha or more, 28.5 g ai/ha or more, 29 g ai/ha or more,29.25 g ai/ha or more, 29.5 g ai/ha or more, or 29.75 g ai/ha or more).

In some embodiments, the tribenuron or agriculturally acceptable salt orester thereof is applied to vegetation or an area adjacent thevegetation or applied to soil or water to prevent the emergence orgrowth of vegetation in an amount of 30 g ai/ha or less (e.g., 29.75 gai/ha or less, 29.5 g ai/ha or less, 29.25 g ai/ha or less, 29 g ai/haor less, 28.5 g ai/ha or less, 28 g ai/ha or less, 27.5 g ai/ha or less,27 g ai/ha or less, 26.5 g ai/ha or less, 26 g ai/ha or less, 25 g ai/haor less, 24 g ai/ha or less, 23 g ai/ha or less, 22 g ai/ha or less, 21g ai/ha or less, 20 g ai/ha or less, 19 g ai/ha or less, 18 g ai/ha orless, 17 g ai/ha or less, 16 g ai/ha or less, 15 g ai/ha or less, 14 gai/ha or less, 13 g ai/ha or less, 12 g ai/ha or less, 11 g ai/ha orless, 10 g ai/ha or less, 9.5 g ai/ha or less, 9 g ai/ha or less, 8.5 gai/ha or less, 8 g ai/ha or less, 7.5 g ai/ha or less, 7 g ai/ha orless, 6.5 g ai/ha or less, 6 g ai/ha or less, 5.75 g ai/ha or less, 5.5g ai/ha or less, 5.25 g ai/ha or less, 5 g ai/ha or less, 4.75 g ai/haor less, 4.5 g ai/ha or less, 4.25 g ai/ha or less, or 4 g ai/ha orless).

The tribenuron or agriculturally acceptable salt or ester thereof can beapplied to vegetation or an area adjacent the vegetation or applied tosoil or water to prevent the emergence or growth of vegetation in anamount ranging from any of the minimum values described above to any ofthe maximum values described above. In some embodiments, the imazamox oragriculturally acceptable salt thereof is applied to vegetation or anarea adjacent the vegetation or applied to soil or water to prevent theemergence or growth of vegetation in an amount of 3.75-30 g ai/ha (e.g.,3.75-29 g ai/ha, 3.75-28 g ai/ha, 3.75-27 g ai/ha, 3.75-25 g ai/ha, 4-30g ai/ha, 4-28 g ai/ha, 4-26 g ai/ha, 4-25 g ai/ha, 5-30 g ai/ha, 5-28 gai/ha, 5-25 g ai/ha, 6-30 g ai/ha, or 6-25 g ai/ha).

II. Compositions

A. Herbicidal Mixtures or Combinations

The (a) pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof is mixed with or applied incombination with (b) an ALS inhibitor or an agriculturally acceptablesalt or ester thereof. In some embodiments, (a) and (b) can be providedin an amount sufficient to induce a herbicidal effect. In someembodiments, (a) and (b) are used in an amount sufficient to induce asynergistic herbicidal effect while still showing good cropcompatibility (i.e., their use in crops does not result in increaseddamage to crops when compared to the individual application of theherbicidal compounds (a) or (b)). As described in the Herbicide Handbookof the Weed Science Society of America, Tenth Edition, 20014, p. 487,“‘synergism’ [is] an interaction of two or more factors such that theeffect when combined is greater than the predicted effect based on theresponse to each factor applied separately.” Synergistic in theherbicide context can mean that the use of (a) and (b) as defined aboveresults in an increased weed control effect compared to the weed controleffects that are possible with the use of (a) or (b) alone. In someembodiments, the damage or injury to the undesired vegetation caused bythe compositions and methods disclosed herein is evaluated using a scalefrom 0% to 100%, when compared with the untreated control vegetation,wherein 0% indicates no damage to the undesired vegetation and 100%indicates complete destruction of the undesired vegetation. In someembodiments, Colby's formula is applied to determine whether using (a)and (b) in combination shows a synergistic effect: S. R. Colby,Calculating Synergistic and Antagonistic Responses of HerbicideCombinations, WEEDS 15, p. 22 (1967)

$E = {X + Y - \frac{X*Y}{100}}$

wherein

X=effect in percent using (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof at anapplication rate a;

Y=effect in percent using (b) an ALS inhibitor or an agriculturallyacceptable salt or ester thereof at an application rate b;

E=expected effect (in %) of (a)+(b) at application rates a and b.

In Colby's equation, the value E corresponds to the effect (plant damageor injury) that is to be expected if the activity of the individualcompounds is additive. If the observed effect is higher than the value Ecalculated according to the Colby equation, then a synergistic effect ispresent according to the Colby equation.

In some embodiments, the compositions and methods disclosed herein aresynergistic as defined by the Colby equation. In some embodiments, thejoint action of a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof and an ALSinhibitor or an agriculturally acceptable salt or ester thereof resultsin enhanced activity against undesired vegetation (via synergism), evenat application rates below those typically used for the pesticide tohave a herbicidal effect on its own. In some embodiments, thecompositions and methods disclosed herein can, based on the individualcomponents, be used at lower application rates to achieve a herbicidaleffect comparable to the effect produced by the individual components atnormal application rates. In some embodiments, the compositions andmethods disclosed herein provide an accelerated action on undesiredvegetation (i.e., they effect damaging of undesired vegetation morequickly compared with application of the individual herbicides).

In some embodiments, the observed effect for undesired vegetation is atleast 1%, at least 2%, at least 3%, at least 4%, at least 5%, at least10%, at least 15%, at least 20%, or at least 25% greater than the effect(E) calculated according to the Colby equation (e.g., an observed effectof 96% would be 4% greater than an calculated effect (E) of 92%). Insome embodiments, for undesired vegetation, the difference (D_(O))between 100% and the observed effect is at least 5%, at least 10%, atleast 15%, at least 20%, at least 25%, at least 30%, at least 35%, atleast 40%, at least 45%, or at least 50% less than the difference(D_(E)) between 100% and the effect (E) calculated according to theColby equation (e.g., an observed effect of 96% would produce a D_(O) of4%, a calculated effect (E) of 92% would produce a D_(E) of 8%, andD_(O) would be 50% less than or half of D_(E)).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) an ALS inhibitor or an agriculturallyacceptable salt or ester thereof (in g ai/ha) is 1:34000 or more (e.g.,1: 3200 or more, 1:3000 or more, 1:2800 or more, 1:2600 or more, 1:2400or more, 1:2200 or more, 1:2000 or more, 1:1800 or more, 1:1600 or more,1:1400 or more, 1:1200 or more, 1:1000 or more, 1:900 or more, 1:800 ormore, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70or more, 1:60 or more, 1:50 or more, 1:40 or more, 1:30 or more, 1:20 ormore, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more,1:5 or more, 1:4 or more, 1:3 or more, 1:2 or more, 1:1.9 or more, 1:1.8or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more,1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more,1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 ormore, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 3:1 ormore, 4:1 or more, 5:1 or more, 6:1 or more, 7:1 or more, 8:1 or more,9:1 or more, 10:1 or more, 20:1 or more, 30:1 or more, 40:1 or more,50:1 or more, 60:1 or more, 70:1 or more, 80:1 or more, 90:1 or more,100:1 or more, 200:1 or more, 300:1 or more, 400:1 or more, 500:1 ormore, 600:1 or more, 700:1 or more, 800:1 or more, 900:1 or more, 1000:1or more, or 1100:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) an ALS inhibitor or an agriculturallyacceptable salt or ester thereof (in g ai/ha) is 1200:1 or less (e.g.,1100:1 or less, 1000:1 or less, 900:1 or less, 800:1 or less, 700:1 orless, 600:1 or less, 500:1 or less, 400:1 or less, 300:1 or less, 200:1or less, 100:1 or less, 90:1 or less, 80:1 or less, 70:1 or less, 60:1or less, 50:1 or less, 40:1 or less, 30:1 or less, 20:1 or less, 10:1 orless, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less,4:1 or less, 3:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less,1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 orless, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 orless, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:3 or less, 1:4 orless, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less,1:10 or less, 1:20 or less, 1:30 or less, 1:40 or less, 1:50 or less,1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less,1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:600 orless, 1:700 or less, 1:800 or less, 1:900 or less, 1:1000 or less,1:1200 or less, 1:1400 or less, 1:1600 or less, 1:1800 or less, 1:2000or less, 1:2200 or less, 1:2400 or less, 1:2600 or less, 1:2800 or less,1:3000 or less, or 1:3200 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof (in g ae/ha)to (b) an ALS inhibitor or an agriculturally acceptable salt or esterthereof (in g ai/ha) can range from any of the minimum ratios describedabove to any of the maximum values described above. In some embodiments,the weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof (in g ae/ha)to (b) an ALS inhibitor or an agriculturally acceptable salt or esterthereof (in g ai/ha) is from 1:34000 to 1200:1 (e.g., from 1:3400 to1000:1, from 1:3200 to 1000:1, from 1:3200 to 800:1, from 1:3000 to600:1, from 1:2500 to 400:1, from 1:2000 to 200:1, from 1:1000 to1200:1, from 1:1000 to 1000:1, from 1:1000 to 100:1, from 1:800 to1000:1, from 1:800 to 800:1, from 1:800 to 400:1, from 1:600 to 600:1,from 1:400 to 400:1, from 1:400 to 200:1, from 1:200 to 200:1, from1:200 to 100:1, from 1:100 to 100:1, from 1:50 to 50:1, from 1:40 to40:1, from 1:30 to 30:1, from 1:20 to 20:1, from 1:10 to 10:1, 1:1000 to20:1, from 1:900 to 10:1, from 1:900 to 50:1, from 1:800 to 40:1, from1:700 to 30:1, from 1:600 to 20:1, from 1:500 to 15:1, from 1:400 to10:1, from 1:300 to 9:1, from 1:200 to 8:1, from 1:100 to 7:1, from 1:50to 6:1, from 1:40 to 5:1, from 1:30 to 4:1, from 1:20 to 3:1, from 1:10to 2:1, from 1:5 to 5:1, from 1:4 to 4:1, from 1:3 to 3:1, or from 1:2to 2:1).

In some embodiments, (b) includes a triazolopyrimidine sulfonamide or anagriculturally acceptable salt or ester thereof. In some embodiments,the weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof (in g ae/ha)to (b) a triazolopyrimidine sulfonamide or an agriculturally acceptablesalt or ester thereof (in g ai/ha) is 1:2000 or more (e.g., 1:1900 ormore, 1:1800 or more, 1:1700 or more, 1:1600 or more, 1:1500 or more,1:1400 or more, 1:1300 or more, 1:1200 or more, 1:1100 or more, 1:1000or more, 1:900 or more, 1:800 or more, 1:700 or more, 1:600 or more,1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 ormore, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 ormore, 1:40 or more, 1:30 or more, 1:20 or more, 1:10 or more, 1:9 ormore, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4 or more,1:3 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more,1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 ormore, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 ormore, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1or more, 1.9:1 or more, 2:1 or more, 3:1 or more, 4:1 or more, 5:1 ormore, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more,20:1 or more, 30:1 or more, 40:1 or more, 50:1 or more, 60:1 or more,70:1 or more, 80:1 or more, 90:1 or more, 100:1 or more, 200:1 or more,300:1 or more, 400:1 or more, 500:1 or more, 600:1 or more, 700:1 ormore, 800:1 or more, 900:1 or more, 1000:1 or more, or 1100:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) a triazolopyrimidine sulfonamide or anagriculturally acceptable salt or ester thereof (in g ai/ha) is 1200:1or less (e.g., 1100:1 or less, 1000:1 or less, 900:1 or less, 800:1 orless, 700:1 or less, 600:1 or less, 500:1 or less, 400:1 or less, 300:1or less, 200:1 or less, 100:1 or less, 90:1 or less, 80:1 or less, 70:1or less, 60:1 or less, 50:1 or less, 40:1 or less, 30:1 or less, 20:1 orless, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less,5:1 or less, 4:1 or less, 3:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less,1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less,1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 orless, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:3 orless, 1:4 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less,1:9 or less, 1:10 or less, 1:20 or less, 1:30 or less, 1:40 or less,1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less,1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 orless, 1:600 or less, 1:700 or less, 1:800 or less, 1:900 or less, 1:1000or less, 1:1100 or less, 1:1200 or less, 1:1300 or less, 1:1400 or less,1:1500 or less, 1:1600 or less, 1:1700 or less, 1:1800 or less, or1:1900 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b) atriazolopyrimidine sulfonamide or an agriculturally acceptable salt orester thereof can range from any of the minimum ratios described aboveto any of the maximum values described above. In some embodiments, theweight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b)triazolopyrimidine sulfonamide or an agriculturally acceptable salt orester thereof is from 1:2000 to 1200:1 (e.g., from 1:2000 to 1000:1,from 1:2000 to 800:1, from 1:2000 to 600:1, from 1:1000 to 400:1, from1:500 to 200:1, from 1:400 to 190:1, from 1:300 to 180:1, from 1:200 to170:1, from 1:50 to 120:1, from 1:1.5 to 150:1, from 1:1.5 to 100:1,from 1:1.5 to 50:1, from 1:10 to 16:1, or from 1:1.5 to 40:1). Incertain embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof to (b) a triazolopyrimidine sulfonamide or an agriculturallyacceptable salt or ester thereof is from 1:3.8 to 16:1, or from 1:5 to6:1.

In some embodiments, (b) includes an imidazolinone or an agriculturallyacceptable salt or ester thereof. In some embodiments, the weight ratioof (a) a pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof (in g ae/ha) to (b)imidazolinone or an agriculturally acceptable salt or ester thereof (ing ai/ha) is 1:3400 or more (e.g., 1: 3200 or more, 1:3000 or more,1:2800 or more, 1:2600 or more, 1:2400 or more, 1:2200 or more, 1:2000or more, 1:1800 or more, 1:1600 or more, 1:1400 or more, 1:1200 or more,1:1000 or more, 1: 900 or more, 1:800 or more, 1:700 or more, 1:600 ormore, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 ormore, 1:40 or more, 1:30 or more, 1:20 or more, 1:10 or more, 1:9 ormore, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4 or more,1:3 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more,1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 ormore, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 ormore, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1or more, 1.9:1 or more, 2:1 or more, 3:1 or more, 4:1 or more, 5:1 ormore, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more,15:1 or more, 20:1 or more, 25:1 or more, 30:1 or more, 35:1 or more,40:1 or more, 45:1 or more, 50:1 or more, 51:1 or more, 52:1 or more,53:1 or more, 54:1 or more, 55:1 or more, 56:1 or more, 57:1 or more,58:1 or more, or 59:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) an imidazolinone or an agriculturallyacceptable salt or ester thereof (in g ai/ha) is 60:1 or less (e.g.,59:1 or less, 58:1 or less, 57:1 or less, 56:1 or less, 55:1 or less,54:1 or less, 53:1 or less, 52:1 or less, 51:1 or less, 50:1 or less,45:1 or less, 40:1 or less, 35:1 or less, 30:1 or less, 25:1 or less,20:1 or less, 15:1 or less, 10:1 or less, 9:1 or less, 8:1 or less, 7:1or less, 6:1 or less, 5:1 or less, 4:1 or less, 3:1 or less, 2:1 orless, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less,1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 orless, 1:2 or less, 1:3 or less, 1:4 or less, 1:5 or less, 1:6 or less,1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:20 or less, 1:30or less, 1:40 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 orless, 1:90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400or less, 1:500 or less, 1:600 or less, 1:700 or less, 1:800 or less,1:900 or less, 1:1000 or less, 1:1200 or less, 1:1400 or less, 1:1600 orless, 1:1800 or less, 1:2000 or less, 1:2200 or less, 1:2400 or less,1:2600 or less, 1:2800 or less, 1:3000 or less, or 1:3200 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b) animidazolinone or an agriculturally acceptable salt or ester thereof canrange from any of the minimum ratios described above to any of themaximum values described above. In some embodiments, the weight ratio of(a) a pyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof to (b) an imidazolinone or anagriculturally acceptable salt or ester thereof is from 1:3400 to 60:1(e.g., from 1:3000 to 60:1, from 1:2500 to 50:1, from 1:2000 to 50:1,from 1:1400 to 60:1, from 1:1500 to 50:1, from 1:1000 to 40:1, from1:750 to 50:1, from 1:440 to 30:1, from 1:280 to 17:1, from 1:100 to15:1, from 1:50 to 10:1, or from 1:50 to 7:1). In certain embodiments,the weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b) animidazolinone or an agriculturally acceptable salt or ester thereof isfrom 1:10 to 5:1, or from 1:10 to 1:6.

In some embodiments, (b) includes pyrimidinyl oxybenzoate or anagriculturally acceptable salt or ester thereof. In some embodiments,the weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof (in g ae/ha)to (b) pyrimidinyl oxybenzoate or an agriculturally acceptable salt orester thereof (in g ai/ha) is 1:600 or more (e.g., 1:590 or more, 1:580or more, 1:570 or more, 1:560 or more, 1:550 or more, 1:500 or more,1:450 or more, 1:400 or more, 1:350 or more, 1:300 or more, 1:250 ormore, 1:225 or more, 1:200 or more, 1:175 or more, 1:150 or more, 1:125or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60or more, 1:50 or more, 1:40 or more, 1:30 or more, 1:20 or more, 1:15 ormore, 1:10 or more, 1:5 or more, 1:2.5 or more, 1:1.25 or more, 1:1.1 ormore, 1:1 or more, 1.1:1 or more, 1.25:1 or more, 1.5:1 or more, 2:1 ormore, 3:1 or more, 4:1 or more, 5:1 or more, 6:1 or more, 7:1 or more,8:1 or more, 9:1 or more, 10:1 or more, 12:1 or more, 14:1 or more, 16:1or more, 18:1 or more, 20:1 or more, 22:1 or more, 24:1 or more, 26:1 ormore, 28:1 or more, 30:1 or more, 32:1 or more, 34:1 or more, 36:1 ormore, 38:1 or more, 40:1 or more, 42:1 or more, 44:1 or more, 46:1 ormore, 48:1 or more, 50:1 or more, 51:1 or more, 52:1 or more, 53:1 ormore, 54:1 or more, 55:1 or more, 56:1 or more, 58:1 or more, or 59:1 ormore).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) a pyrimidinyl oxybenzoate or anagriculturally acceptable salt or ester thereof (in g ai/ha) is 60:1 orless (e.g., 59:1 or less, 58:1 or less, 57:1 or less, 56:1 or less, 55:1or less, 54:1 or less, 53:1 or less, 52:1 or less, 51:1 or less, 50:1 orless, 48:1 or less, 46:1 or less, 44:1 or less, 42:1 or less, 40:1 orless, 38:1 or less, 36:1 or less, 34:1 or less, 32:1 or less, 30:1 orless, 28:1 or less, 26:1 or less, 24:1 or less, 22:1 or less, 20:1 orless, 18:1 or less, 16:1 or less, 14:1 or less, 12:1 or less, 10:1 orless, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less,4:1 or less, 3:1 or less, 2:1 or less, 1.5:1 or less, 1.25:1 or less,1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.25 or less, 1:2.5 orless, 1:5 or less, 1:10 or less, 1:15 or less, 1:20 or less, 1:30 orless, 1:40 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 orless, 1:90 or less, 1:100 or less, 1:125 or less, 1:150 or less, 1:175or less, 1:200 or less, 1:225 or less, 1:250 or less, 1:300 or less,1:350 or less, 1:400 or less, 1:450 or less, 1:500 or less, 1:550 orless, 1:560 or less, 1:570 or less, 1:580 or less, or 1:590 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b) apyrimidinyl oxybenzoate or an agriculturally acceptable salt or esterthereof can range from any of the minimum ratios described above to anyof the maximum values described above. In some embodiments, the weightratio of (a) a pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof to (b) a pyrimidinyloxybenzoate or an agriculturally acceptable salt thereof is from 1:600to 60:1 (e.g., from 1:500 to 60:1, from 1:500 to 55:1, from 1:400 to52:1, from 1:400 to 50:1, from 1:300 to 47:1, from 1:250 to 45:1, from1:200 to 42:1, from 1:140 to 40:1, from 1:130 to 30:1, 1:120 to 20:1 orfrom 1:100 to 10:1). In certain embodiments, the weight ratio of (a) apyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof to (b) a pyrimidinyl oxybenzoate or anagriculturally acceptable salt or ester thereof is from 1:15 to 5:1, orfrom 1:10 to 5:1.

In some embodiments, (b) includes a sulfonylaminocarbonyl triazolinoneor an agriculturally acceptable salt or ester thereof. In someembodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) sulfonylaminocarbonyl triazolinone or anagriculturally acceptable salt or ester thereof (in g ai/ha) is 1:600 ormore (e.g., 1:590 or more, 1:580 or more, 1:570 or more, 1:560 or more,1:550 or more, 1:500 or more, 1:450 or more, 1:400 or more, 1:350 ormore, 1:300 or more, 1:250 or more, 1:225 or more, 1:200 or more, 1:175or more, 1:150 or more, 1:125 or more, 1:100 or more, 1:90 or more, 1:80or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:40 or more, 1:30 ormore, 1:20 or more, 1:15 or more, 1:10 or more, 1:5 or more, 1:2.5 ormore, 1:1.25 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.25:1or more, 1.5:1 or more, 2:1 or more, 3:1 or more, 4:1 or more, 5:1 ormore, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more,12:1 or more, 14:1 or more, 16:1 or more, 18:1 or more, 20:1 or more,25:1 or more, 30:1 or more, 35:1 or more, 40:1 or more, 45:1 or more,50:1 or more, 55:1 or more, 60:1 or more, 65:1 or more, 70:1 or more,75:1 or more, 80:1 or more, 85:1 or more, 90:1 or more, 95:1 or more,100:1 or more, 105:1 or more, 110:1 or more, 112:1 or more, 114:1 ormore, 116:1 or more, 117:1 or more, 118:1 or more, or 119:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) a sulfonylaminocarbonyl triazolinone or anagriculturally acceptable salt or ester thereof (in g ai/ha) is 120:1 orless (e.g., 119:1 or less, 118:1 or less, 117:1 or less, 116:1 or less,114:1 or less, 112:1 or less, 110:1 or less, 105:1 or less, 100:1 orless, 95:1 or less, 90:1 or less, 85:1 or less, 80:1 or less, 75:1 orless, 70:1 or less, 65:1 or less, 60:1 or less, 55:1 or less, 50:1 orless, 45:1 or less, 40:1 or less, 35:1 or less, 30:1 or less, 25:1 orless, 20:1 or less, 18:1 or less, 16:1 or less, 14:1 or less, 12:1 orless, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less,5:1 or less, 4:1 or less, 3:1 or less, 2:1 or less, 1.5:1 or less,1.25:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.25 orless, 1:2.5 or less, 1:5 or less, 1:10 or less, 1:15 or less, 1:20 orless, 1:30 or less, 1:40 or less, 1:50 or less, 1:60 or less, 1:70 orless, 1:80 or less, 1:90 or less, 1:100 or less, 1:125 or less, 1:150 orless, 1:175 or less, 1:200 or less, 1:225 or less, 1:250 or less, 1:300or less, 1:350 or less, 1:400 or less, 1:450 or less, 1:500 or less,1:550 or less, 1:560 or less, 1:570 or less, 1:580 or less, or 1:590 orless).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b) asulfonylaminocarbonyl triazolinone or an agriculturally acceptable saltor ester thereof can range from any of the minimum ratios describedabove to any of the maximum values described above. In some embodiments,the weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b)sulfonylaminocarbonyl triazolinone or an agriculturally acceptable saltor ester thereof is from 1:600 to 120:1 (e.g., from 1:500 to 120:1, from1:500 to 100:1, from 1:400 to 100:1, from 1:400 to 80:1, from 1:300 to120:1, from 1:300 to 100:1, from 1:250 to 120:1, from 1:200 to 100:1,from 1:175 to 85:1, from 1:150 to 80:1, from 1:140 to 80:1, from 1:130to 50:1, or from 1:100 to 25:1). In certain embodiments, the weightratio of (a) a pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof to (b) sulfonylaminocarbonyltriazolinone or an agriculturally acceptable salt or ester thereof isfrom 1:7.5 to 10:1, or from 1:5 to 1:1.

In some embodiments, (b) includes sulfonylurea or an agriculturallyacceptable salt or ester thereof. In some embodiments, the weight ratioof (a) a pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof (in g ae/ha) to (b) asulfonylurea or an agriculturally acceptable salt thereof (in g ai/ha)is 1:400 or more (e.g., 1:390 or more, 1:380 or more, 1:360 or more,1:360 or more, 1:350 or more, 1:340 or more, 1:330 or more, 1:320 ormore, 1:310 or more, 1:300 or more, 1:250 or more, 1:225 or more, 1:200or more, 1:175 or more, 1:150 or more, 1:125 or more, 1:100 or more,1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more,1:40 or more, 1:30 or more, 1:20 or more, 1:15 or more, 1:10 or more,1:5 or more, 1:2.5 or more, 1:1.25 or more, 1:1.1 or more, 1:1 or more,1.1:1 or more, 1.25:1 or more, 2.5:1 or more, 5:1 or more, 10:1 or more,15:1 or more, 20:1 or more, 30:1 or more, 40:1 or more, 50:1 or more,60:1 or more, 70:1 or more, 80:1 or more, 90:1 or more, 100:1 or more,125:1 or more, 150:1 or more, 175:1 or more, 200:1 or more, 225:1 ormore, 250:1 or more, 300:1 or more, 310:1 or more, 320:1 or more, 330:1or more, 340:1 or more, 350:1 or more, 360:1 or more, 380:1 or more,385:1 or more, 390:1 or more, 392:1 or more, 394:1 or more, 396:1 ormore, 397:1 or more, 398:1 or more, or 399:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof (in g ae/ha) to (b) a sulfonylurea or an agriculturallyacceptable salt or ester thereof (in g ai/ha) is 400:1 or less (e.g.,390:1 or less, 380:1 or less, 370:1 or less, 360:1 or less, 350:1 orless, 340:1 or less, 330:1 or less, 320:1 or less, 310:1 or less, 300:1or less, 250:1 or less, 225:1 or less, 200:1 or less, 175:1 or less,150:1 or less, 125:1 or less, 100:1 or less, 90:1 or less, 80:1 or less,70:1 or less, 60:1 or less, 50:1 or less, 40:1 or less, 30:1 or less,20:1 or less, 15:1 or less, 10:1 or less, 5:1 or less, 2.5:1 or less,1.25:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.25 orless, 1:2.5 or less, 1:5 or less, 1:10 or less, 1:15 or less, 1:20 orless, 1:30 or less, 1:40 or less, 1:50 or less, 1:60 or less, 1:70 orless, 1:80 or less, 1:90 or less, 1:100 or less, 1:125 or less, 1:150 orless, 1:175 or less, 1:200 or less, 1:225 or less, 1:250 or less, 1:300or less, 1:310 or less, 1:320 or less, 1:330 or less, 1:340 or less,1:350 or less, 1:360 or less, or 1:390 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof to (b) asulfonylurea or an agriculturally acceptable salt or ester thereof canrange from any of the minimum ratios described above to any of themaximum values described above. In some embodiments, the weight ratio of(a) a pyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof to (b) a sulfonylurea or anagriculturally acceptable salt or ester thereof is from 1:400 to 400:1(e.g., from 1:300 to 300:1, from 1:250 to 250:1, from 1:200 to 200:1,from 1:175 to 175:1, from 1:150 to 150:1, from 1:125 to 125:1, from1:100 to 100:1, from 1:75 to 75:1, from 1:50 to 50:1, from 1:40 to 40:1,from 1:30 to 30:1, from 1:25 to 25:1, or from 1:20 to 20:1). In certainembodiments, the weight ratio of (a) a pyridine carboxylic acidherbicide or an agriculturally acceptable N-oxide, salt, or esterthereof to (b) sulfonylurea or an agriculturally acceptable salt thereofis from 1:10 to 5:1, or from 1:8.75 to 2:1.

In some embodiments, the active ingredients in the compositionsdisclosed herein consist of (a) a pyridine carboxylic acid herbicide oran agriculturally acceptable N-oxide, salt, or ester thereof and (b) anALS inhibitor or an agriculturally acceptable salt or ester thereof.

B. Formulations

The present disclosure also relates to formulations of the compositionsand methods disclosed herein. In some embodiments, the formulation canbe in the form of a single package formulation including both (a) apyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof and (b) an ALS inhibitor or anagriculturally acceptable salt or ester thereof. In some embodiments,the formulation can be in the form of a single package formulationincluding both (a) and (b) and further including at least one additive.In some embodiments, the formulation can be in the form of a two-packageformulation, wherein one package contains (a) and optionally at leastone additive while the other package contains (b) and optionally atleast one additive. In some embodiments of the two-package formulation,the formulation including (a) and optionally at least one additive andthe formulation including (b) and optionally at least one additive aremixed before application and then applied simultaneously. In someembodiments, the mixing is performed as a tank mix (i.e., theformulations are mixed immediately before or upon dilution with water).In some embodiments, the formulation including (a) and the formulationincluding (b) are not mixed but are applied sequentially (insuccession), for example, immediately or within 1 hour, within 2 hours,within 4 hours, within 8 hours, within 16 hours, within 24 hours, within2 days, or within 3 days, of each other.

In some embodiments, the formulation of (a) and (b) is present insuspended, emulsified, or dissolved form. Exemplary formulationsinclude, but are not limited to, aqueous solutions, powders,suspensions, also highly-concentrated aqueous, oily or other suspensionsor dispersions, aqueous emulsions, aqueous microemulsions, aqueoussuspo-emulsions, oil dispersions, self-emulsifying formulations, pastes,dusts, and materials for spreading or granules.

In some embodiments, (a) a pyridine carboxylic acid herbicide or anagriculturally acceptable N-oxide, salt, or ester thereof and/or (b) anALS inhibitor or an agriculturally acceptable salt or ester thereof isan aqueous solution that can be diluted before use. In some embodiments,(a) and/or (b) is provided as a high-strength formulation such as aconcentrate. In some embodiments, the concentrate is stable and retainspotency during storage and shipping. In some embodiments, theconcentrate is a clear, homogeneous liquid that is stable attemperatures of 54° C. or greater. In some embodiments, the concentratedoes not exhibit any precipitation of solids at temperatures of −10° C.or higher. In some embodiments, the concentrate does not exhibitseparation, precipitation, or crystallization of any components at lowtemperatures. For example, the concentrate remains a clear solution attemperatures below 0° C. (e.g., below −5° C., below −10° C., below −15°C.). In some embodiments, the concentrate exhibits a viscosity of lessthan 50 centipoise (50 megapascals), even at temperatures as low as 5°C.

The compositions and methods disclosed herein can also be mixed with orapplied with an additive. In some embodiments, the additive can bediluted in water or can be concentrated. In some embodiments, theadditive is added sequentially. In some embodiments, the additive isadded simultaneously. In some embodiments, the additive is premixed withthe pyridine carboxylic acid herbicide or agriculturally acceptableN-oxide, salt, or ester thereof. In some embodiments, the additive ispremixed with the ALS inhibitor or agriculturally acceptable salt orester thereof.

C. Other Actives

In some embodiments, the additive is an additional pesticide. Forexample, the compositions described herein can be applied in conjunctionwith one or more additional herbicides to control undesirablevegetation. The composition can be formulated with the one or moreadditional herbicides, tank mixed with the one or more additionalherbicides, or applied sequentially with the one or more additionalherbicides. Exemplary additional herbicides include, but are not limitedto: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 2,4-D choline salt, 2,4-D esters andamines, 2,4-DB, 3,4-DA, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA,2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein,alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione,ametryn, amibuzin, amicarbazone, aminocyclopyrachlor, 4-aminopicolinicacid based herbicides, such as halauxifen, halauxifen-methyl,4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylicacis, benzyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate,and those described in U.S. Pat. Nos. 7,314,849 and 7,432,227 to Balko,et al., aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate,anilofos, anisuron, asulam, atraton, atrazine, azafenidin, aziprotryne,barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin,benfuresate, bensulide, benthiocarb, bentazon-sodium, benzadox,benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor,benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, borax,bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil,brompyrazon, butachlor, butafenacil, butamifos, butenachlor,buthidazole, buthiuron, butralin, butroxydim, buturon, butylate,cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide,cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb,carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben,chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam,chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol,chloridazon, chlomitrofen, chloropon, chlorotoluron, chloroxuron,chloroxynil, chlorpropham, chlorthal, chlorthiamid, cinidon-ethyl,cinmethylin, cisanilide, clacyfos, clethodim, cliodinate,clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop,cloproxydim, clopyralid, CMA, copper sulfate, CPMF, CPPC, credazine,cresol, cumyluron, cyanatryn, cyanazine, cycloate, cycloxydim, cycluron,cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromid, daimuron,dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba,dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P,diclofop-methyl, diethamquat, diethatyl, difenopenten, difenoxuron,difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate,dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano,dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb,dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron,DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon,esprocarb, ethalfluralin, ethbenzamide, ethidimuron, ethiolate,ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, etinofen,etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop,fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone,fenquinotrione, fenteracol, fenthiaprop, fentrazamide, fenuron, ferroussulfate, flamprop, flamprop-M, fluazifop, fluazifop-P-butyl, fluazolate,fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumezin,flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen,fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam,flupropacil, flupropanate, fluridone, flurochloridone, fluroxypyr,fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, fosamine,fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium,glufosinate-P-ammonium, glyphosate salts and esters, halosafen,haloxydine, hexachloroacetone, hexaflurate, hexazinone, indanofan,indaziflam, iodobonil, iodomethane, ioxynil, ipazine, ipfencarbazone,iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen,lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl,MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide,mesoprazine, mesotrione, metam, metamifop, metamitron, metazachlor,metflurazon, methabenzthiazuron, methalpropalin, methazole,methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methylbromide, methyl isothiocyanate, methyldymron, metobenzuron,metobromuron, metolachlor, metoxuron, metribuzin, molinate, monalide,monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat,MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon,nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron,OCH, orbencarb, ortho-dichlorobenzene, oryzalin, oxadiargyl, oxadiazon,oxapyrazon, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron,paraquat, pebulate, pelargonic acid, pendimethalin, pentachlorophenol,pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham,phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate,picloram, picolinafen, pinoxaden, piperophos, potassium arsenite,potassium azide, potassium cyanate, pretilachlor, procyazine,prodiamine, profluazol, profluralin, profoxydim, proglinazine,prohexadione-calcium, prometon, prometryn, pronamide, propachlor,propanil, propaquizafop, propazine, propham, propisochlor, propyzamide,prosulfalin, prosulfocarb, proxan, prynachlor, pydanon, pyraclonil,pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen,pyributicarb, pyriclor, pyridafol, pyridate, quinclorac, quinmerac,quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil,saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim,siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodiumazide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone,sulfosate, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron,tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb,terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron,thenylchlor, thiameturon, thiazafluron, thiazopyr, thidiazimin,thidiazuron, thiobencarb, tiafenacil, tiocarbazil, tioclorim,tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone,triaziflam, tricamba, triclopyr choline salt, triclopyr esters andamines, tridiphane, trietazine, trifludimoxazin, trifluralin, trifop,trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac,vemolate, xylachlor and salts, esters, optically active isomers, andmixtures thereof.

In some embodiments, the additional pesticide or an agriculturallyacceptable salt or ester thereof is provided in a premixed formulationwith (a), (b), or combinations thereof. In some embodiments, thepyridine carboxylic acid herbicide or an agriculturally acceptableN-oxide, salt, or ester thereof is provided in a premixed formulationwith an additional pesticide. In some embodiments, the ALS inhibitor oran agriculturally acceptable salt or ester thereof is provided in apremixed formulation with an additional pesticide. In some embodiments,the florasulam the cloransulam, the diclosulam, the flumetsulam, themetosulam, the penoxsulam, the pyroxsulam, or an agriculturallyacceptable salt thereof, is provided in a premixed formulation with anadditional pesticide. In some embodiments, the imazamethabenz, theimazamox, the imazapic, the imazapyr, the imazaquin, the imazethapyr, oran agriculturally acceptable salt or ester thereof, is provided in apremixed formulation with an additional pesticide. In some embodiments,the bispyribac, the pyribenzoxim, the pyriftalid, the pyriminobac, thepyrimisulfan, the pyrithiobac, or an agriculturally acceptable salt orester thereof, is provided in a premixed formulation with an additionalpesticide. In some embodiments, the flucarbazone, the propoxycarbazone,the thiencarbazone, or an agriculturally acceptable salt or esterthereof, is provided in a premixed formulation with an additionalpesticide. In some embodiments, the amidosulfuron, the azimsulfuron, thebensulfuron, the chlorimuron, the chlorsulfuron, the cinosulfuron, thecyclosulfamuron, the ethametsulfuron, the ethoxysulfuron, theflazasulfuron, the flucetosulfuron, the flupyrsulfuron, theforamsulfuron, the halosulfuron, the imazosulfuron, the iodosulfuron,the iofensulfuron, the mesosulfuron, the metazosulfuron, themetsulfuron, the nicosulfuron, the orthosulfamuron, the oxasulfuron, theprimisulfuron, the propyrisulfuron, the prosulfuron, the pyrazosulfuron,the rimsulfuron, the sulfometuron, the sulfosulfuron, the triasulfuron,the tribenuron, the thifensulfuron, the trifloxysulfuron, thetriflusulfuron, the tritosulfuron, or an agriculturally acceptable saltor ester thereof, is provided in a premixed formulation with anadditional pesticide.

D. Adjuvants/Carriers/Colorants/Adhesives

In some embodiments, the additive includes an agriculturally acceptableadjuvant. Exemplary agriculturally acceptable adjuvants include, but arenot limited to, antifreeze agents, antifoam agents, compatibilizingagents, sequestering agents, neutralizing agents and buffers, corrosioninhibitors, colorants, odorants, penetration aids, wetting agents,spreading agents, dispersing agents, thickening agents, freeze pointdepressants, antimicrobial agents, crop oil, herbicide safeners,adhesives (for instance, for use in seed formulations), surfactants,protective colloids, emulsifiers, tackifiers, and mixtures thereof.

Exemplary agriculturally acceptable adjuvants include, but are notlimited to, crop oil concentrate (mineral oil (85%) +emulsifiers (15%));nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammoniumsalt; blend of petroleum hydrocarbon, alkyl esters, organic acid, andanionic surfactant; C₉-C₁₁ alkylpolyglycoside; phosphate alcoholethoxylate; natural primary alcohol (C₁₂-C₁₆) ethoxylate or less,di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated seedoil; tridecyl alcohol (synthetic) ethoxylate (8 EO); tallow amineethoxylate (15 EO); and PEG(400) dioleate-99.

In some embodiments, the additive is a safener, which is an organiccompound leading to better crop plant compatibility when applied with aherbicide. In some embodiments, the safener itself is herbicidallyactive. In some embodiments, the safener acts as an antidote orantagonist in the crop plants and can reduce or prevent damage to thecrop plants. Exemplary safeners include, but are not limited to, AD-67(MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl),cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon,dietholate, dimepiperate, disulfoton, fenchlorazole,fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole,harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr,mefenpyr-diethyl, mephenate, naphthalic anhydride,2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine,(dichloroacetyl)-1-oxa-4-azaspiro [4.5]decane, oxabetrinil, R29148, andN-phenyl-sulfonylbenzoic acid amides, as well as thereof agriculturallyacceptable salts and, provided they have a carboxyl group, theiragriculturally acceptable derivatives. In some embodiments, the safenercan be cloquintocet or an ester or salt or ester thereof, such ascloquintocet (mexyl). In some embodiments, the safener can bedichlormid. In some embodiments, the safener is employed in rice,cereal, or maize. For example, dichlormid or cloquintocet can be used toantagonize harmful effects of the compositions on rice, row crops, andcereals.

Exemplary surfactants (e.g., wetting agents, tackifiers, dispersants,emulsifiers) include, but are not limited to, the alkali metal salts,alkaline earth metal salts and ammonium salts of aromatic sulfonicacids, for example lignosulfonic acids, phenolsulfonic acids,naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid, and offatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene or of the naphthalene sulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl ortributylphenyl polyglycol ether, alkyl aryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors and proteins, denatured proteins,polysaccharides (e.g., methylcellulose), hydrophobically modifiedstarches, polyvinyl alcohol, polycarboxylates, polyalkoxylates,polyvinyl amine, polyethyleneimine, polyvinylpyrrolidone and copolymersthereof.

Exemplary thickeners include, but are not limited to, polysaccharides,such as xanthan gum, and organic and inorganic sheet minerals, andmixtures thereof.

Exemplary antifoam agents include, but are not limited to, siliconeemulsions, long-chain alcohols, fatty acids, salts of fatty acids,organofluorine compounds, and mixtures thereof.

Exemplary antimicrobial agents include, but are not limited to,bactericides based on dichlorophen and benzyl alcohol hemiformal, andisothiazolinone derivatives, such as alkylisothiazolinones andbenzisothiazolinones, and mixtures thereof.

Exemplary antifreeze agents, include, but are not limited to ethyleneglycol, propylene glycol, urea, glycerol, and mixtures thereof.

Exemplary colorants include, but are not limited to, the dyes knownunder the names Rhodamine B, pigment blue 15:4, pigment blue 15:3,pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1,pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1,pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange34, pigment orange 5, pigment green 36, pigment green 7, pigment white6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acidred 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basicred 108, and mixtures thereof.

Exemplary adhesives include, but are not limited to,polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, andmixtures thereof.

In some embodiments, the additive includes a carrier. In someembodiments, the additive includes a liquid or solid carrier. In someembodiments, the additive includes an organic or inorganic carrier.Exemplary liquid carriers include, but are not limited to, petroleumfractions or hydrocarbons such as mineral oil, aromatic solvents,paraffinic oils, and the like or less, vegetable oils such as soybeanoil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconutoil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil,safflower oil, sesame oil, tung oil and the like or less, esters of theabove vegetable oils or less, esters of monoalcohols or dihydric,trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propyleneglycol dioleate, di-octyl succinate, di-butyl adipate, di-octylphthalate and the like or less, esters of mono, di and polycarboxylicacids and the like, toluene, xylene, petroleum naphtha, crop oil,acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene,perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propyleneglycol monomethyl ether and diethylene glycol monomethyl ether, methylalcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethyleneglycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone,N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and thelike, and water as well as mixtures thereof. Exemplary solid carriersinclude, but are not limited to, silicas, silica gels, silicates, talc,kaolin, limestone, lime, chalk, bole, loess, clay, dolomite,diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide,ground synthetic materials, pyrophyllite clay, attapulgus clay,kieselguhr, calcium carbonate, bentonite clay, Fuller's earth,cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnutshell flour, lignin, ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas, cereal meal, tree bark meal, wood meal and nutshellmeal, cellulose powders, and mixtures thereof.

In some embodiments, emulsions, pastes or oil dispersions can beprepared by homogenizing (a) and (b) in water by means of wetting agent,tackifier, dispersant or emulsifier. In some embodiments, concentratessuitable for dilution with water are prepared, comprising (a), (b), awetting agent, a tackifier, and a dispersant or emulsifier.

In some embodiments, powders or materials for spreading and dusts can beprepared by mixing or concomitant grinding of (a) and (b) and optionallya safener with a solid carrier.

In some embodiments, granules (e.g., coated granules, impregnatedgranules and homogeneous granules) can be prepared by binding the (a)and (b) to solid carriers.

The formulations disclosed herein can comprise a synergistic,herbicidally effective amount of (a) and (b). In some embodiments, theconcentrations of (a) and (b) in the formulations can be varied. In someembodiments, the formulations comprise from 1% to 95% (e.g., from 5% to95%, from 10% to 80%, from 20% to 70%, from 30% to 50%) by total weightof (a) and (b). In formulations designed to be employed as concentrates,(a) and (b) can be present in a concentration of from 0.1 to 98 weightpercent (0.5 to 90 weight percent), based on the total weight of theformulation. Concentrates can be diluted with an inert carrier, such aswater, prior to application. The diluted formulations applied toundesired vegetation or the locus of undesired vegetation can containfrom 0.0006 to 8.0 weight percent of (a) and (b) (e.g., from 0.001 to5.0 weight percent), based on the total weight of the dilutedformulation.

In some embodiments, (a) and (b), independently, can be employed in apurity of from 90% to 100% (e.g., from 95% to 100%) according to nuclearmagnetic resonance (NMR) spectrometry. In some embodiments, theconcentrations of (a), (b), and additional pesticides in theformulations can be varied. In some embodiments, the formulationscomprise from 1% to 95% (e.g., from 5% to 95%, from 10% to 80%, from 20%to 70%, from 30% to 50%) by total weight of (a), (b), and additionalpesticides. In some embodiments, (a), (b), and additional pesticides,independently, can be employed in a purity of from 90% to 100% (e.g.,from 95% to 100%) according to NMR spectrometry.

III. Methods of Use

A. Methods of Application

The compositions disclosed herein can be applied in any known techniquefor applying herbicides. Exemplary application techniques include, butare not limited to, spraying, atomizing, dusting, spreading, or directapplication into water (in-water). The method of application can varydepending on the intended purpose. In some embodiments, the method ofapplication can be chosen to ensure the finest possible distribution ofthe compositions disclosed herein.

In some embodiments, a method of controlling undesirable vegetationwhich comprises contacting the vegetation or the locus thereof with orapplying to the soil or water to prevent the emergence or growth ofvegetation any of the compositions is disclosed herein.

The compositions disclosed herein can be applied pre-emergence (beforethe emergence of undesirable vegetation) or post-emergence (i.e., duringand/or after emergence of the undesirable vegetation). If desired, thecompositions can be applied as an in-water application. In someembodiments, the pyridine carboxylic acid or an agriculturallyacceptable N-oxide, salt, or ester thereof and the ALS inhibitor or anagriculturally acceptable salt or ester thereof are appliedsimultaneously.

When the compositions are used in crops, the compositions can be appliedafter seeding and before or after the emergence of the crop plants. Insome embodiments, the compositions disclosed herein show good croptolerance even when the crop has already emerged and can be appliedduring or after the emergence of the crop plants. In some embodiments,when the compositions are used in crops, the compositions can be appliedbefore seeding of the crop plants.

In some embodiments, the compositions disclosed herein are applied tovegetation or an area adjacent the vegetation or applied to soil orwater to prevent the emergence or growth of vegetation by spraying(e.g., foliar spraying). In some embodiments, the spraying techniquesuse, for example, water as carrier and spray liquor rates of from 10liters per hectare (L/ha) to 2000 L/ha (e.g., from 50 L/ha to 1000 L/ha,or from 100 to 500 L/ha). In some embodiments, the compositionsdisclosed herein are applied by the low-volume or the ultra-low-volumemethod, wherein the application is in the form of micro granules. Insome embodiments, wherein the compositions disclosed herein are lesswell tolerated by certain crop plants, the compositions can be appliedwith the aid of the spray apparatus in such a way that they come intolittle contact, if any, with the leaves of the sensitive crop plantswhile reaching the leaves of undesirable vegetation that growsunderneath or the bare soil (e.g., post-directed or lay-by). In someembodiments, the compositions disclosed herein can be applied as dryformulations (e.g., granules, WDGs, etc.) into water.

In some embodiments, herbicidal activity is exhibited by the compoundsof the mixture when they are applied directly to the plant or to thelocus of the plant at any stage of growth or before planting oremergence. The effect observed can depend upon the type of undesirablevegetation to be controlled, the stage of growth of the undesirablevegetation, the application parameters of dilution and spray drop size,the particle size of solid components, the environmental conditions atthe time of use, the specific compound employed, the specific adjuvantsand carriers employed, the soil type, and the like, as well as theamount of chemical applied. In some embodiments, these and other factorscan be adjusted to promote non-selective or selective herbicidal action.In some cases, the compositions are applied to relatively immatureundesirable vegetation.

The compositions and methods disclosed herein can be used to controlundesired vegetation in a variety of crop and non-crop applications. Insome embodiments, the compositions and methods disclosed herein can beused for controlling undesired vegetation in crops. Exemplary cropsinclude, but are not limited to, wheat, barley, triticale, rye, teff,oats, maize, cotton, soy, sorghum, rice, sugarcane and range land (e.g.,pasture grasses). In some embodiments, the undesirable vegetation iscontrolled in a row crop (e.g., maize, sorghum, soybean, cotton, oroilseed rape/canola). In some embodiments, the compositions and methodsdisclosed herein can be used for controlling undesired vegetation inmaize, wheat, rice, barley, or a combination thereof.

The compositions and methods disclosed herein can be used forcontrolling undesired vegetation in non-crop areas. Exemplary non-cropareas include, but are not limited to, turfgrass, pastures, grasslands,fallow land, rights-of-way, aquatic settings, tree and vine, wildlifemanagement areas, or rangeland. In some embodiments, the compositionsand methods disclosed herein can be used in industrial vegetationmanagement (IVM) or for utility, pipeline, roadside, and railroadrights-of-way applications. In some embodiments, the compositions andmethods disclosed herein can also be used in forestry (e.g., for sitepreparation or for combating undesirable vegetation in plantationforests). In some embodiments, the compositions and methods disclosedherein can be used to control undesirable vegetation in conservationreserve program lands (CRP), trees, vines, grasslands, and grasses grownfor seeds. In some embodiments, the compositions and methods disclosedherein can be used on lawns (e.g., residential, industrial, andinstitutional), golf courses, parks, cemeteries, athletic fields, andsod farms.

The compositions and methods disclosed herein can also be used in cropplants that are resistant to, for instance, herbicides, pathogens,and/or insects. In some embodiments, the compositions and methodsdisclosed herein can be used in crop plants that are resistant to one ormore herbicides because of genetic engineering or breeding. In someembodiments, the compositions and methods disclosed herein can be usedin crop plants that are resistant to one or more pathogens such as plantpathogenous fungi owing to genetic engineering or breeding. In someembodiments, the compositions and methods disclosed herein can be usedin crop plants that are resistant to attack by insects owing to geneticengineering or breeding. Exemplary resistant crops include, but are notlimited to, crops that are resistant to photosystem II inhibitors, orcrop plants that, owing to introduction of the gene for Bacillusthuringiensis (or Bt) toxin by genetic modification, are resistant toattack by certain insects. In some embodiments, the compositions andmethods described herein also can be used in conjunction withglyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins,aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,protoporphyrinogen oxidase (PPO) inhibitors, triazines, and bromoxynilto control vegetation in crops tolerant to glyphosate, glufosinate,dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates,acetyl CoA carboxylase (ACCase) inhibitors, 4-hydroxyphenyl-pyruvatedioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PPO)inhibitors, triazines, bromoxynil, or combinations thereof. In someembodiments, the undesirable vegetation is controlled in glyphosate,glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins,aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors,4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,protoporphyrinogen oxidase (PPO) inhibitors, triazines, and bromoxyniltolerant crops possessing single, multiple or stacked traits conferringtolerance to single or multiple chemistries and/or multiple modes ofaction. In some embodiments, the undesirable vegetation can becontrolled in a crop that is ACCase-tolerant. The combination of (a),(b), and a complementary herbicide or salt or ester thereof can be usedin combination with herbicides that are selective for the crop beingtreated and which complement the spectrum of weeds controlled by thesecompounds at the application rate employed. In some embodiments, thecompositions described herein and other complementary herbicides areapplied at the same time, either as a combination formulation or as atank mix, or as sequential applications.

The compositions and methods may be used in controlling undesirablevegetation in crops possessing agronomic stress tolerance (including butnot limited to drought, cold, heat, salt, water, nutrient, fertility,pH), pest tolerance (including but not limited to insects, fungi andpathogens) and crop improvement traits (including but not limited toyield; protein, carbohydrate, or oil content; protein, carbohydrate, oroil composition; plant stature and plant architecture).

In some embodiments, the compositions disclosed herein can be used forcontrolling undesirable vegetation including grasses, broadleaf weeds,sedge weeds, and combinations thereof. In some embodiments, thecompositions disclosed herein can be used for controlling undesirablevegetation including, but not limited to, Polygonum species such as wildbuckwheat (Polygonum convolvulus), Alopecurus species such as blackgrass(Alopecurus myosuroides), Amaranthus species such as pigweed (Amaranthusretroflexus), Avena species such as wild oat (Avena fatua) Chenopodiumspecies such as common lambsquarters (Chenopodium album L.), Sidaspecies such as prickly sida (Sida spinosa L.), Ambrosia species such ascommon ragweed (Ambrosia artemisiifolia), Cyperus species such asnutsedge (Cyperus esculentus), Setaria species such as giant foxtail(Setaria faberi), Sorghum species, Acanthospermum species, Anthemisspecies, Atriplex species, Brassica species, Cirsium species,Convolvulus species, Conyza species, such as horseweed (Conyzacanadensis), Cassia species, Commelina species, Datura species,Digitaria species such as large crabgrass (Digitaria sanguinalis),Echinola species such as barnyardgrass (Echinola crus-galli) Euphorbiaspecies, Geranium species, Galinsoga species, Ipomoea species such asivyleaf morning-glory (Ipomoea hederacea), Lamium species, Malvaspecies, Matricaria species, Persicaria species, Prosopis species, Rumexspecies, Sisymbrium species, Solanum species, Trifolium species,Xanthium species, Veronica species, Viola species such as wild pansy(Viola tricolor), common chickweed (Stellaria media), velvetleaf(Abutilon theophrasti), hemp sesbania (Sesbania exaltata Cory), Anodacristata, Bidens pilosa, Brassica kaber, shepherd's purse (Capsellabursa-pastoris), cornflower (Centaurea cyanus or Cyanus segetum),Galeopsis tetrahit, cleavers (Galium aparine), Helianthus annuus,Desmodium tortuosum, kochia (Kochia scoparia), Medicago arabica,Mercurialis annua, Myosotis arvensis, common poppy (Papaver rhoeas),Raphanus raphanistrum, Russian thistle (Salsola kali), wild mustard(Sinapis arvensis), Sonchus arvensis, Thlaspi arvense, Tagetes minuta,Richardia brasiliensis, Plantago major, Plantago lanceolata, bird's-eyespeedwell (Veronica persica) and speedwell.

In certain embodiments, the undesirable vegetation includes velvetleaf(Abutilon theophrasti, ABUTH), blackgrass (Alopecurus myosuroides,ALOMY), pigweed (Amaranthus retrollexus, AMARE), wild oat (Avena fatua,AVEFA), brown mustard (Brassica juncea, BRSJU), rutabaga (Brassica napusvar. napobrassica, BRSNA), spring rape (Brassica napus, BRSNN), winterrape (Brassica napus, BRSNW), turnip (Brassica rapa, BRSRR), commonlambsquarters (Chenopodium album L., CHEAL), thistle (Cirsium arvenseCIRAR), nutsedge (Cyperus esculentus, CYPES), large crabgrass (Digitariasanguinalis, DIGSA), barnyardgrass (Echinochloa crus-galli, ECHCG),poinsettia (Euphorbia heterophylla, EPHHL), soybean (Glycine max,GLXMA), sunflower (Helianthus annuus, HELAN), ivyleaf morning-glory(Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), wildbuckwheat (Polygonum convolvulus, POLCO), giant foxtail (Setaria faberi,SETFA), grain sorghum (Sorghum vulgare, SORVU), common chickweed(Stellaria media, STEME), wild pansy (Viola tricolor, VIOTR), or acombination thereof. In certain embodiments, the undesirable vegetationincludes poinsettia (Euphorbia heterophylla, EPHHL), nutsedge (Cyperusesculentus, CYPES), or a combination thereof.

The herbicidal compositions described herein can be used to controlherbicide resistant or tolerant weeds. The methods employing thecompositions described herein may also be employed to control herbicideresistant or tolerant weeds. Exemplary resistant or tolerant weedsinclude, but are not limited to, biotypes resistant or tolerant toacetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS)inhibitors (e.g., imidazolinones, sulfonylureas,pyrimidinyl(oxy/thio)benzoates, sulfonylaminocarbonyltriazolinones),photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones,triazines, triazinones, uracils, amides, ureas, benzothiadiazinones,nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors(e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines),synthetic auxins (e.g., benzoic acids, phenoxycarboxylic acids, pyridinecarboxylic acids, quinoline carboxylic acids), auxin transportinhibitors (e.g., phthalamates, semicarbazones), photosystem Iinhibitors (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate(EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetaseinhibitors (e.g., glufosinate, bialafos), microtubule assemblyinhibitors (e.g., benzamides, benzoic acids, dinitroanilines,phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates),very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides,chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipidsynthesis inhibitors (e.g., phosphorodithioates, thiocarbamates,benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO)inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles,oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles,triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone,amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g.,amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones,pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors(e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulosebiosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac,triazolocarboxamides), herbicides with multiple modes-of-action such asquinclorac, and unclassified herbicides such as arylaminopropionicacids, difenzoquat, endothall, and organoarsenicals. Exemplary resistantor tolerant weeds include, but are not limited to, biotypes withresistance or tolerance to multiple herbicides, biotypes with resistanceor tolerance to multiple chemical classes, biotypes with resistance ortolerance to multiple herbicide modes-of-action, and biotypes withmultiple resistance or tolerance mechanisms (e.g., target siteresistance or metabolic resistance).

By way of non-limiting illustration, examples of certain embodiments ofthe present disclosure are given below.

EXAMPLES Example 1 Herbicidal Activity and Effect on Crop Injury onWinter Wheat of Compounds of Formula (I) and TriazolopyrimidineSulfonamide Herbicides in Greenhouse Trials Methodology—Evaluation ofPostemergence Herbicidal Activity in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Spray solutions of theexperimental compound mixtures were prepared by adding the stocksolutions to the appropriate amount of dilution solution to form a 12 mLspray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. Applicationrates for component (a) are in g ae/ha, and application rates forcomponent (b) are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

Compound 2 was combined with florasulam and applied to winter wheat(TRZAW) and the phytotoxicity of the herbicidal composition wasmeasured. In addition, the efficacy of the herbicidal composition onpoinsettia (Euphorbia heterophylla, EPHHL) and water grass (Cyperusesculentus, CYPES) was evaluated. The results are summarized in Table 1.

TABLE 1 Effect (% visual injury) of compound 2 and florasulam on weeds.Application Rate Compound 2 (g ae/ha) 5 10 0 5 10 Florasulam (g ai/ha) 00 1.25 1.25 1.25 EPHHL Obs 35 75 0 100 90 Exp — — — 35 75 Δ 65 15 CYPESObs 5 10 15 18 53 Exp — — — 19 24 Δ −2 29 TRZAW Obs 3 3 0 0 3 Exp — — —3 3 Δ −3 0 g ae/ha = grams acid equivalent per hectare; g ai/ha = gramsactive ingredient per hectare; EPHHL = Euphorbia heterophylla(poinsettia); CYPES = Cyperus esculentus (nutsedge); TRZAW = Triticumaestivum (winter wheat)

Example 2 Herbicidal Activity and Effect on Crop Injury on Winter Wheat,Common Rice and Maize of Compounds of Formula (I) and TriazolopyrimidineSulfonamide Herbicides in Greenhouse Trials Methodology—Evaluation ofPostemergence Herbicidal Activity in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical or formulated material (emulsifiableconcentrate (EC) or soluble concentrate (SL)) were dissolved in a volumeof 97:3 volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) tostock solutions. If the experimental compound did not dissolve readily,the mixture was warmed and/or sonicated. The concentrated stocksolutions were diluted with an aqueous mixture of 1.5% v/v of Agri-dexcrop oil concentrate to provide the appropriate application rates.Compound requirements are based upon a 12 milliliter (mL) applicationvolume at a rate of 187 liters per hectare (L/ha). Spray solutions ofthe experimental compound mixtures were prepared by adding the stocksolutions to the appropriate amount of dilution solution to form a 12 mLspray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. Applicationrates for component (a) are in g ae/ha, and application rates forcomponent (b) are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

Compound 1 was formulated as an EC and was combined with florasulam,cloransulam, diclosulam, flumetsulam, penoxsulam, or pyroxsulam.Compound 2 was formulated as an EC and was combined with florasulam orpyroxsulam. The mixtures were applied to winter wheat (TRZAW), commonrice (ORYSA), maize (ZEAMX), and the phytotoxicity of the herbicidalcompositions was measured. In addition, the efficacy of the herbicidalcompositions on blackgrass (Alopecurus myosuroides, ALOMY), pigweed(Amaranthus retrollexus, AMARE), wild oat (Avena fatua, AVEFA), commonlambsquarters (Chenopodium album L., CHEAL), thistle (Cirsium arvenseCIRAR), nutsedge (Cyperus esculentus, CYPES), barnyardgrass (Echinochloacrus-galli, ECHCG), poinsettia (Euphorbia heterophylla, EPHHL), ivyleafmorning-glory (Ipomoea hederacea, IPOHE), kochia (Kochia scoparia,KCHSC), wild buckwheat (Polygonum convolvulus, POLCO), grain sorghum(Sorghum vulgare, SORVU), chickweed (Stellaria media, STEME), wild pansy(Viola tricolor, VIOTR), was evaluated. The results are summarized inTables 2-9.

TABLE 2 Effect (% visual injury) of compound 2 and florasulam on weeds.Application Rate Compound 2 (g ae/ha) 5 10 0 5 10 Florasulam (g ai/ha) 00 1.25 1.25 1.25 AMARE Obs 88 100 75 100 100 Exp 97 100 Δ 3 0 CHEAL Obs88 99 0 90 100 Exp 88 99 Δ 3 1 IPOHE Obs 10 20 98 100 100 Exp 98 98 Δ 22 ORYSA Obs 10 18 0 3 13 Exp 10 18 Δ −8 −5 ZEAMX Obs 3 3 0 0 3 Exp 3 3 Δ−3 0 g ae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare AMARE = Amaranthus retroflexus (pigweed) CHEAL =Chenopodium album L. (common lambsquarters) IPOHE = Ipomoea hederacea(ivy leaf morning-glory) ORYSA = Oryza sativa (common rice) ZEAMX = Zeamays (maize)

TABLE 3 Effect (% visual injury) of compound 1 and florasulam on weeds.Compound 1 (g ae/ha) 5 0 5 Florasulam (g ai/ha) Application Rate 0 2.52.5 CYPES Obs 10 75 85 Exp 78 Δ 8 KCHSC Obs 65 60 95 Exp 86 Δ 9 ORYSAObs 0 0 0 Exp 0 Δ 0 TRZAW Obs 5 0 0 Exp 5 Δ −5 ZEAMX Obs 0 0 0 Exp 0 Δ 0g ae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare CYPES = Cyperus esculentus (nutsedge) KCHSC =Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) TRZAW =Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 4 Effect (% visual injury) of compound 1 and cloransulam on weeds.Compound 1 (g ae/ha) 5 0 5 Cloransulam (g ai/ha) Application Rate 04.375 4.375 AMARE Obs 95 0 100 Exp 95 Δ 5 CHEAL Obs 80 0 85 Exp 80 Δ 5CIRAR Obs 10 99 100 Exp 99 Δ 1 CYPES Obs 10 50 70 Exp 55 Δ 15 EPHHL Obs97 30 100 Exp 98 Δ 2 KCHSC Obs 65 0 90 Exp 65 Δ 25 POLCO Obs 70 85 100Exp 96 Δ 5 STEME Obs 50 0 70 Exp 50 Δ 20 TRZAW Obs 5 10 0 Exp 15 Δ −15 gae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare AMARE = Amaranthus retroflexus (pigweed) CHEAL =Chenopodium album L. (common lambsquarters) CIRAR = Cirsium arvense(thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbiaheterophylla (poinsettia) KCHSC = Kochia scoparia (kochia) POLCO =Polygonum convolvulus (wild buckwheat) STEME = Stellaria media(chickweed) TRZAW = Triticum aestivum (winter wheat)

TABLE 5 Effect (% visual injury) of compound 1 and diclosulam on weeds.Compound 1 (g ae/ha) 5 0 5 Diclosulam (g ai/ha) Application Rate 0 4.3754.375 AMARE Obs 95 60 100 Exp 98 Δ 2 CHEAL Obs 80 0 85 Exp 80 Δ 5 CIRARObs 10 93 100 Exp 94 Δ 6 CYPES Obs 10 50 60 Exp 55 Δ 5 ECHCG Obs 50 3080 Exp 65 Δ 15 EPHHL Obs 97 60 100 Exp 99 Δ 1 IPOHE Obs 30 93 100 Exp 95Δ 5 KCHSC Obs 65 50 93 Exp 83 Δ 11 STEME Obs 50 0 70 Exp 50 Δ 20 TRZAWObs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare g ai/ha= grams active ingredient per hectare AMARE = Amaranthus retroflexus(pigweed) CHEAL = Chenopodium album L. (common lambsquarters) CIRAR =Cirsium arvense (thistle) CYPES = Cyperus esculentus (nutsedge) ECHCG =Echinochloa crus-galli (barnyardgrass) EPHHL = Euphorbia heterophylla(poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morning-glory) KCHSC =Kochia scoparia (kochia) STEME = Stellaria media (chickweed) TRZAW =Triticum aestivum (winter wheat)

TABLE 6 Effect (% visual injury) of compound 1 and flumetsulam on weeds.Compound 1 (g ae/ha) 5 0 5 Flumetsulam (g ai/ha) Application Rate 04.375 4.375 CIRAR Obs 10 10 65 Exp 19 Δ 46 CYPES Obs 10 10 60 Exp 19 Δ41 EPHHL Obs 97 30 100 Exp 98 Δ 2 KCHSC Obs 65 60 93 Exp 86 Δ 7 SORVUObs 10 60 65 Exp 64 Δ 1 VIOTR Obs 30 70 80 Exp 79 Δ 1 ORYSA Obs 0 0 0Exp 0 Δ 0 TRZAW Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent perhectare g ai/ha = grams active ingredient per hectare CIRAR = Cirsiumarvense (thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL =Euphorbia heterophylla (poinsettia) KCHSC = Kochia scoparia (kochia)SORVU = Sorghum vulgare (grain sorghum) VIOTR = Viola tricolor (wildpansy) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum(winter wheat)

TABLE 7 Effect (% visual injury) of compound 2 and pyroxsulam on weeds.Application Rate Compound 2 (g ae/ha) 5 10 0 5 10 Pyroxsulam (g ai/ha) 00 3.75 3.75 3.75 ALOMY Obs 0 0 10 10 25 Exp 10 10 Δ 0 15 AVEFA Obs 0 060 65 60 Exp 60 60 Δ 5 0 CYPES Obs 5 10 23 33 40 Exp 26 30 Δ 6 10 IPOHEObs 10 20 83 68 95 Exp 84 86 Δ −17 9 ORYSA Obs 10 18 33 35 30 Exp 39 44Δ −4 −14 TRZAW Obs 3 3 0 0 0 Exp 3 3 Δ −3 −3 g ae/ha = grams acidequivalent per hectare g ai/ha = grams active ingredient per hectareALOMY = Alopecurus myosuroides (blackgrass) AVEFA = Avena fatua (wildoat) CYPES = Cyperus esculentus (nutsedge) IPOHE = Ipomoea hederacea(ivy leaf morning-glory) ORYSA = Oryza sativa (common rice) TRZAW =Triticum aestivum (winter wheat)

TABLE 8 Effect (% visual injury) of compound 1 and penoxsulam on weeds.Compound 1 (g ae/ha) 5 0 5 Penoxsulam (g ai/ha) Application Rate 0 5 5CYPES Obs 10 70 90 Exp 73 Δ 17 EPHHL Obs 97 60 100 Exp 99 Δ 1 IPOHE Obs30 90 100 Exp 93 Δ 7 KCHSC Obs 65 10 93 Exp 69 Δ 25 SORVU Obs 10 0 20Exp 10 Δ 10 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 5 10 0 Exp 15 Δ −15 gae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare CYPES = Cyperus esculentus (nutsedge) EPHHL =Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleafmorning-glory) KCHSC = Kochia scoparia (kochia) SORVU = Sorghum vulgare(grain sorghum) ORYSA = Oryza sativa (common rice) TRZAW = Triticumaestivum (winter wheat)

TABLE 9 Effect (% visual injury) of compound 1 and pyroxsulam on weeds.Compound 1 (g ae/ha) 5 0 5 Pyroxsulam (g ai/ha) Application Rate 04.6875 4.6875 CIRAR Obs 10 90 93 Exp 91 Δ 2 CYPES Obs 10 65 75 Exp 69 Δ7 ECHCG Obs 50 93 97 Exp 97 Δ 1 IPOHE Obs 30 95 100 Exp 97 Δ 4 KCHSC Obs65 50 95 Exp 83 Δ 13 POLCO Obs 70 85 97 Exp 96 Δ 2 ORYSA Obs 0 30 25 Exp30 Δ −5 TRZAW Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent perhectare g ai/ha = grams active ingredient per hectare CIRAR = Cirsiumarvense (thistle) CYPES = Cyperus esculentus (nutsedge) ECHCG =Echinochloa crus-galli (barnyardgrass) IPOHE = Ipomoea hederacea(ivyleaf morning-glory) KCHSC = Kochia scoparia (kochia) POLCO =Polygonum convolvulus (wild buckwheat) ORYSA = Oryza sativa (commonrice) TRZAW = Triticum aestivum (winter wheat)

Example 3 Herbicidal Activity and Effect on Crop Injury on Winter Wheatof Compounds of Formula (I) and Imidazolinone Herbicides in GreenhouseTrials Methodology—Evaluation of Postemergence Herbicidal Activity inCrops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Spray solutions of theexperimental compound mixtures were prepared by adding the stocksolutions to the appropriate amount of dilution solution to form a 12 mLspray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. Applicationrates for component (a) are in g ae/ha, and application rates forcomponent (b) are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

Compound 1 was formulated as an EC and was combined with imazamox,imazamethabenz, imazapic, imazapyr or imazethapyr. The mixtures wereapplied to winter wheat (TRZAW) and/or maize (ZEAMX), and thephytotoxicity of the herbicidal compositions was measured. In addition,the efficacy of the herbicidal compositions on blackgrass (Alopecurusmyosuroides, ALOMY), wild oat (Avena fatua, AVEFA), winter rape(Brassica napus, BRSNW), spring rape (Brassica napus, BRSNN), turnip(Brassica rapa, BRSRR), thistle (Cirsium arvense, CIRAR), largecrabgrass (Digitaria sanguinalis, DIGSA), pigweed (Amaranthusretrollexus, AMARE), common lambsquarters (Chenopodium album L., CHEAL),poinsettia (Euphorbia heterophylla, EPHHL), ivyleaf morning-glory(Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), wildbuckwheat (Polygonum convolvulus, POLCO), grain sorghum (Sorghumvulgare, SORVU), chickweed (Stellaria media, STEME), wild pansy (Violatricolor, VIOTR), sunflower (Helianthus annuus, HELAN), giant foxtail(Setaria faberi, SETFA), soybean (Glycine max, GLXMA), rutabaga(Brassica napus var. napobrassica, BRSNA) and barnyardgrass (Echinochloacrus-galli, ECHCG) was evaluated. The results are summarized in Tables10-14.

TABLE 10 Effect (% visual injury) of compound 1 and imazamox on weeds.Compound 1 (g ae/ha) 5 0 5 Imazamox (g ai/ha) Application Rate 0 11.211.2 BRSNN Obs 50 75 95 Exp 88 Δ 8 BRSRR Obs 50 70 100 Exp 85 Δ 15 CIRARObs 10 70 85 Exp 73 Δ 12 POLCO Obs 65 65 90 Exp 88 Δ 2 g ae/ha = gramsacid equivalent per hectare g ai/ha = grams active ingredient perhectare BRSNN = Brassica napus (spring rape) BRSRR = Brassica rapa(turnip) CIRAR = Cirsium arvense (thistle) POLCO = Polygonum convolvulus(wild buckwheat)

TABLE 11 Effect (% visual injury) of compound 1 and imazethapyr onweeds. Compound 1 (g ae/ha) 5 0 5 Imazethapyr (g ai/ha) Application Rate0 17.5 17.5 ALOMY Obs 0 10 20 Exp 10 Δ 10 AVEFA Obs 0 10 50 Exp 10 Δ 40BRSNW Obs 30 75 95 Exp 83 Δ 13 BRSNA Obs 65 20 75 Exp 72 Δ 3 CIRAR Obs10 30 70 Exp 37 Δ 33 DIGSA Obs 5 30 70 Exp 34 Δ 37 ECHCG Obs 70 70 95Exp 91 Δ 4 VIOTR Obs 5 5 25 Exp 10 Δ 15 g ae/ha = grams acid equivalentper hectare g ai/ha = grams active ingredient per hectare ALOMY =Alopecurus myosuroides (blackgrass) AVEFA = Avena fatua (wild oat) BRSNW= Brassica napus (winter rape) BRSNA = Brassica napus var. napobrassica(rutabaga) CIRAR = Cirsium arvense (thistle) DIGSA = Digitariasanguinalis (large crabgrass) ECHCG = Echinochloa crus-galli(barnyardgrass) VIOTR = Viola tricolor (wild pansy)

TABLE 12 Effect (% visual injury) of compound 1 and imazamethabenz onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Imazamethabenz(g ai/ha) 0 0 100 100 100 AMARE Obs 75 97 0 100 100 Exp 75 97 Δ 25 3AVEFA Obs 0 0 20 40 30 Exp 20 20 Δ 20 10 BRSNW Obs 40 45 65 75 90 Exp 7981 Δ −4 9 CHEAL Obs 90 100 20 93 100 Exp 92 100 Δ 1 0 ECHCG Obs 20 60 530 60 Exp 24 62 Δ 6 −2 EPHHL Obs 97 97 50 100 100 Exp 99 99 Δ 2 2 GLXMAObs 95 100 30 100 100 Exp 97 100 Δ 4 0 HELAN Obs 90 90 5 95 95 Exp 91 91Δ 5 5 IPOHE Obs 10 10 0 10 20 Exp 10 10 Δ 0 10 KCHSC Obs 60 60 0 60 65Exp 60 60 Δ 0 5 SORVU Obs 0 50 0 10 30 Exp 0 50 Δ 10 −20 STEME Obs 70 7010 65 75 Exp 73 73 Δ −8 2 TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 ZEAMX Obs 00 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare; gai/ha = grams active ingredient per hectare; AMARE = Amaranthusretroflexus (pigweed); AVEFA = Avena fatua (wild oat); BRSNW = Brassicanapus (winter rape); CHEAL = Chenopodium album L. (commonlambsquarters); ECHCG = Echinochloa crus-galli (barnyardgrass); EPHHL =Euphorbia heterophylla (poinsettia); GLXMA = Glycine max (soybean);HELAN = Helianthus annuus (sunflower); IPOHE = Ipomoea hederacea(ivyleaf morning-glory); KCHSC = Kochia scoparia (kochia); SORVU =Sorghum vulgare (grain sorghum); STEME = Stellaria media (chickweed);TRZAW = Triticum aestivum (winter wheat); ZEAMX = Zea mays (maize)

TABLE 13 Effect (% visual injury) of compound 1 and imazapic on weeds.Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Imazapic (g ai/ha) 0 035 35 35 AVEFA Obs 0 0 95 100 97 Exp 95 95 Δ 5 2 ECHCG Obs 20 60 93 100100 Exp 94 97 Δ 6 3 IPOHE Obs 10 10 75 100 65 Exp 78 78 Δ 23 −13 SETFAObs 10 50 90 95 95 Exp 91 95 Δ 4 0 VIOTR Obs 5 10 10 20 50 Exp 15 19 Δ 631 g ae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare AVEFA = Avena faints (wild oat) ECHCG =Echinochloa crus-galli (barnyardgrass) IPOHE = Ipomoea hederacea (ivyleaf morning-glory) SETFA = Setaria faberi (giant foxtail) VIOTR = Violatricolor (wild pansy)

TABLE 14 Effect (% visual injury) of compound 1 and imazapyr on weeds.Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Imazapyr (g ai/ha) 0 0280 280 280 ALOMY Obs 0 0 97 100 100 Exp 97 97 Δ 3 3 DIGSA Obs 0 10 9597 97 Exp 95 96 Δ 2 2 IPOHE Obs 10 10 85 90 100 Exp 87 87 Δ 4 14 VIOTRObs 5 10 80 85 93 Exp 81 82 Δ 4 11 g ae/ha = grams acid equivalent perhectare g ai/ha = grams active ingredient per hectare ALOMY = Alopecurusmyosuroides (blackgrass) DIGSA = Digitaria sanguinalis (large crabgrass)IPOHE = Ipomoea hederacea (ivy leaf morning-glory) VIOTR = Violatricolor (wild pansy)

Example 4 Herbicidal Activity and Effect on Crop Injury on Winter Wheator Common Rice of Compounds of Formula (I) and Pyrimidinyl OxybenzoatesHerbicides in Greenhouse Trials Methodology—Evaluation of PostemergenceHerbicidal Activity in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Spray solutions of theexperimental compound mixtures were prepared by adding the stocksolutions to the appropriate amount of dilution solution to form a 12 mLspray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. Applicationrates for component (a) are in g ae/ha, and application rates forcomponent (b) are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

Compound 1 was formulated as an EC and was combined withbispyribac-sodium or pyribenzoxim. The mixtures were applied to commonrice (ORYSA), and the phytotoxicity of the herbicidal compositions wasmeasured In addition, the efficacy of the herbicidal composition onthistle (Cirsium arvense, CIRAR), velvetleaf (Abutilon theophrasti,ABUTH), large crabgrass (Digitaria sanguinalis, DIGSA), ivyleafmorning-glory (Ipomoea hederacea, IPOHE), kochia (Kochia scoparia,KCHSC), giant foxtail (Setaria faberi, SETFA), chickweed (Stellariamedia, STEME) and wild pansy (Viola tricolor, VIOTR) was evaluated. Theresults are summarized in Tables 15 and 16.

TABLE 15 Effect (% visual injury) of compound 1 and bispyribac-sodium onweeds. Compound 1 (g ae/ha) 5 0 5 Bispyribac-sodium (g ai/ha)Application Rate 0 10 10 CIRAR Obs 10 95 97 Exp 96 Δ 2 VIOTR Obs 5 80 90Exp 81 Δ 9 ORYSA Obs 5 10 15 Exp 15 Δ 1 g ae/ha = grams acid equivalentper hectare g ai/ha = grams active ingredient per hectare CIRAR =Cirsium arvense (thistle) VIOTR = Viola tricolor (wild pansy) ORYSA =Oryza sativa (common rice)

TABLE 16 Effect (% visual injury) of compound 1 and pyribenzoxim onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Pyribenzoxim (gai/ha) 0 0 15 15 15 ABUTH Obs 50 60 10 65 80 Exp 55 64 Δ 10 16 DIGSA Obs0 10 0 0 20 Exp 0 10 Δ 0 10 IPOHE Obs 10 10 70 90 93 Exp 73 73 Δ 17 20KCHSC Obs 60 60 0 85 65 Exp 60 60 Δ 25 5 SETFA Obs 10 50 70 93 80 Exp 7385 Δ 20 −5 STEME Obs 70 70 40 60 90 Exp 82 82 Δ −22 8 ORYSA Obs 0 10 010 10 Exp 0 10 Δ 10 0 g ae/ha = grams acid equivalent per hectare gai/ha = grams active ingredient per hectare ABUTH = Abutilon theophrasti(velvetleaf) DIGSA = Digitaria sanguinalis (large crabgrass) IPOHE =Ipomoea hederacea (ivyleaf morning-glory) KCHSC = Kochia scoparia(kochia) SETFA = Setaria faberi (giant foxtail) STEME = Stellaria media(chickweed) ORYSA = Oryza sativa (common rice)

Example 5 Herbicidal Activity and Effect on Crop Injury on Winter Wheatof Compounds of Formula (I) and Sulfonylaminocarbonyl TriazolinoneHerbicides in Greenhouse Trials Methodology—Evaluation of PostemergenceHerbicidal Activity in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Spray solutions of theexperimental compound mixtures were prepared by adding the stocksolutions to the appropriate amount of dilution solution to form a 12 mLspray solution in two-way combinations. Formulated compounds wereapplied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. Applicationrates for component (a) are in g ae/ha, and application rates forcomponent (b) are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

Compound 1 was formulated as an EC and was combined with flucarbazone,propoxycarbazone, or thiencarbazone. The mixtures were applied to winterwheat (TRZAW), common rice (Oryza sativa, ORYSA) and/or maize (Zea mays,ZEAMX), and the phytotoxicity of the herbicidal compositions wasmeasured. In addition, the efficacy of the herbicidal compositions onvelvetleaf (Abutilon theophrasti, ABUTH), wild oat (Avena fatua, AVEFA),common lambsquarters (Chenopodium album L., CHEAL), thistle (Cirsiumarvense, CIRAR), nutsedge (Cyperus esculentus, CYPES), large crabgrass(Digitaria sanguinalis, DIGSA), barnyardgrass (Echinochloa crus-galli,ECHCG), sunflower (Helianthus annuus, HELAN), ivyleaf morning-glory(Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), wildbuckwheat (Polygonum convolvulus, POLCO), common chickweed (Stellariamedia, STEME), and wild pansy (Viola tricolor, VIOTR) was evaluated. Theresults are summarized in Tables 17-19.

TABLE 17 Effect (% visual injury) of compound 1 and flucarbazone onweeds. Compound 1 (g ae/ha) 5 0 5 Flucarbazone (g ai/ha) ApplicationRate 0 7.5 7.5 ABUTH Obs 70 30 97 Exp 79 Δ 18 CIRAR Obs 10 85 90 Exp 87Δ 4 CYPES Obs 10 0 70 Exp 10 Δ 60 DIGSA Obs 0 60 65 Exp 60 Δ 5 KCHSC Obs65 20 90 Exp 72 Δ 18 STEME Obs 50 40 85 Exp 70 Δ 15 ORYSA Obs 0 50 40Exp 50 Δ −10 TRZAW Obs 5 10 10 Exp 15 Δ −5 g ae/ha = grams acidequivalent per hectare g ai/ha = grams active ingredient per hectareABUTH = Abutilon theophrasti (velvetleaf) CIRAR = Cirsium arvense(thistle) CYPES = Cyperus esculentus (nutsedge) DIGSA = Digitariasanguinalis (large crabgrass) KCHSC = Kochia scoparia (kochia) STEME =Stellaria media (chickweed) ORYSA = Oryza sativa (common rice) TRZAW =Triticum aestivum (winter wheat)

TABLE 18 Effect (% visual injury) of compound 1 and propoxycarbazone onweeds. Compound 1 (g ae/ha) 5 0 5 Propoxycarbazone (g ai/ha) ApplicationRate 0 7.5 7.5 ABUTH Obs 70 50 95 Exp 85 Δ 10 AVEFA Obs 0 85 93 Exp 85 Δ8 CHEAL Obs 80 30 93 Exp 86 Δ 7 CIRAR Obs 10 75 93 Exp 78 Δ 16 CYPES Obs10 75 85 Exp 78 Δ 8 ECHCG Obs 50 95 100 Exp 98 Δ 3 HELAN Obs 90 85 100Exp 99 Δ 2 IPOHE Obs 30 95 100 Exp 97 Δ 4 KCHSC Obs 65 30 90 Exp 76 Δ 15POLCO Obs 70 10 100 Exp 73 Δ 27 STEME Obs 50 50 97 Exp 75 Δ 22 VIOTR Obs30 20 60 Exp 44 Δ 16 TRZAW Obs 5 10 10 Exp 15 Δ −5 g ae/ha = grams acidequivalent per hectare; g ai/ha = grams active ingredient per hectare;ABUTH = Abutilon theophrasti (velvetleaf); AVEFA = Avena fatua (wildoat); CHEAL = Chenopodium album L. (common lambsquarters); CIRAR =Cirsium arvense (thistle); CYPES = Cyperus esculentus (nutsedge); ECHCG= Echinochloa crus-galli (barnyardgrass); HELAN = Helianthus annuus(sunflower); IPOHE = Ipomoea hederacea (ivyleaf morning-glory); KCHSC =Kochia scoparia (kochia); POLCO = Polygonum convolvulus (wildbuckwheat); STEME = Stellaria media (common chickweed); VIOTR = Violatricolor (wild pansy); TRZAW = Triticum aestivum (winter wheat)

TABLE 19 Effect (% visual injury) of compound 1 and thiencarbazone onweeds. Compound 1 (g ae/ha) 5 0 5 Thiencarbazone (g ai/ha) ApplicationRate 0 5 5 CIRAR Obs 10 50 80 Exp 55 Δ 25 CYPES Obs 10 70 80 Exp 73 Δ 7KCHSC Obs 65 10 93 Exp 69 Δ 25 STEME Obs 50 95 100 Exp 98 Δ 3 TRZAW Obs5 0 0 Exp 5 Δ −5 ZEAMX Obs 0 10 10 Exp 10 Δ 0 g ae/ha = grams acidequivalent per hectare g ai/ha = grams active ingredient per hectareCIRAR = Cirsium arvense (thistle) CYPES = Cyperus esculentus (nutsedge)KCHSC = Kochia scoparia (kochia) STEME = Stellaria media (chickweed)TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

Example 6 Herbicidal Activity and Effect on Crop Injury on Winter Wheat,Common Rice and Maize of Compounds of Formula (I) and SulfonylureaHerbicides in Greenhouse Trials Methodology—Evaluation of PostemergenceHerbicidal Activity in Crops: Greenhouse Trials

Seeds of the desired test plant species were planted in Sun GroMetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8and an organic matter content of about 30 percent, in plastic pots witha surface area of 103.2 square centimeters (cm²). When required toensure good germination and healthy plants, a fungicide treatment and/orother chemical or physical treatment was applied. The plants were grownfor 7-36 days (d) in a greenhouse with an approximate 14-hour (h)photoperiod which was maintained at about 23° C. during the day and 22°C. during the night. Nutrients and water were added on a regular basisand supplemental lighting was provided with overhead metal halide1000-Watt lamps as necessary. The plants were employed for testing whenthey reached the second or third true leaf stage.

Weighed amounts of technical material were dissolved in a volume of 97:3volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stocksolutions. If the experimental compound did not dissolve readily, themixture was warmed and/or sonicated. The concentrated stock solutionswere diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oilconcentrate to provide the appropriate application rates. Compoundrequirements are based upon a 12 milliliter (mL) application volume at arate of 187 liters per hectare (L/ha). Spray solutions of theexperimental compound mixtures were prepared by adding the stocksolutions to the appropriate amount of dilution solution to form a 12 mLspray solution in two- and three-way combinations. Formulated compoundswere applied to the plant material with an overhead Mandel track sprayerequipped with 8002E nozzles calibrated to deliver 187 L/ha over anapplication area of 0.503 square meters (m²) at a spray height of 18inches (43 centimeters (cm)) above average plant canopy. Control plantswere sprayed in the same manner with the solvent blank. Applicationrates for component (a) are in g ae/ha, and application rates forcomponent (b) are in g ai/ha.

The treated plants and control plants were placed in a greenhouse asdescribed above and watered by sub-irrigation to prevent wash-off of thetest compounds. After 20-22 d, the condition of the test plants ascompared with that of the control plants was determined visually andscored on a scale of 0 to 100 percent where 0 corresponds to no injuryand 100 corresponds to complete kill. The condition of the test plantswas compared with that of the control plants as determined visually andscored on a scale of 0 to 100 percent, where 0 corresponds to no injuryand 100 corresponds to complete kill. Colby's equation was used todetermine the herbicidal effects expected from the mixtures.

Compound 1 was formulated as an EC and was combined with amidosulfuron,azimsulfuron, bensulfuron, ethoxysulfuron, foramsulfuron chlorsulfuron,flupyrsulfuron, halosulfuron, iodosulfuron, mesosulfuron, metsulfuron,nicosulfuron, orthosulfamuron, sulfosulfuron, thifensulfuron, ortribenuron, and Compound 1 was formulated as an EC and was combined withmesosulfuron+iodosulfuron or thifensulfuron+tribenuron. The mixtureswere applied to winter wheat (TRZAW), maize (ZEAMX) and/or common rice(ORYSA), and the phytotoxicity of the herbicidal compositions wasmeasured. In addition, the efficacy of the herbicidal compositions onvelvetleaf (Abutilon theophrasti, ABUTH), blackgrass (Alopecurusmyosuroides, ALOMY), pigweed (Amaranthus retrollexus, AMARE), brownmustard (Brassica juncea, BRSJU), spring rape (Brassica napus, BRSNN),winter rape (Brassica napus, BRSNW), lambsquarters (Chenopodium albumL., CHEAL), thistle (Cirsium arvense CIRAR), nutsedge (Cyperusesculentus, CYPES), barnyardgrass (Echinochloa crus-galli, ECHCG),poinsettia (Euphorbia heterophylla, EPHHL), common sunflower (Helianthusannuus, HELAN), ivyleaf morning-glory (Ipomoea hederacea, IPOHE), kochia(Kochia scoparia, KCHSC), wild buckwheat (Polygonum convolvulus, POLCO),giant foxtail (Setaria faberi, SETFA), grain sorghum (Sorghum vulgare,SORVU), common chickweed (Stellaria media, STEME), wild pansy (Violatricolor, VIOTR) and was evaluated. The results are summarized in Tables20-38.

TABLE 20 Effect (% visual injury) of compound 1 and amidosulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Amidosulfuron (g ai/ha) ApplicationRate 0 7.5 7.5 CIRAR Obs 10 20 70 Exp 28 Δ 42 CYPES Obs 10 20 50 Exp 28Δ 22 ECHCG Obs 50 0 70 Exp 50 Δ 20 IPOHE Obs 30 35 65 Exp 55 Δ 11 KCHSCObs 65 10 75 Exp 69 Δ 7 POLCO Obs 70 85 100 Exp 96 Δ 5 ORYSA Obs 0 0 0Exp 0 Δ 0 TRZAW Obs 5 0 10 Exp 5 Δ 5 ZEAMX Obs 0 0 10 Exp 0 Δ 10 g ae/ha= grams acid equivalent per hectare g ai/ha = grams active ingredientper hectare CIRAR = Cirsium arvense (thistle) CYPES = Cyperus esculentus(nutsedge) ECHCG = Echinochloa crus-galli (barnyardgrass) IPOHE =Ipomoea hederacea (ivyleaf morning-glory) KCHSC = Kochia scoparia(kochia) POLCO = Polygonum convolvulus (wild buckwheat) ORYSA = Oryzasativa (common rice) TRZAW = Triticum aestivum (winter wheat) ZEAMX =Zea mays (maize)

TABLE 21 Effect (% visual injury) of compound 1 and azimsulfuron onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Azimsulfuron (gai/ha) 0 0 6.25 6.25 6.25 CHEAL Obs 90 100 10 95 93 Exp 91 100 Δ 4 −7EPHHL Obs 97 97 10 100 100 Exp 97 97 Δ 3 3 IPOHE Obs 10 10 93 97 100 Exp94 94 Δ 3 6 KCHSC Obs 60 60 0 65 70 Exp 60 60 Δ 5 10 SORVU Obs 0 50 6570 80 Exp 65 83 Δ 5 −3 STEME Obs 70 70 20 95 85 Exp 76 76 Δ 19 9 VIOTRObs 5 10 60 70 75 Exp 62 64 Δ 8 11 ORYSA Obs 0 10 0 0 0 Exp 0 10 Δ 0 −10TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent perhectare g ai/ha = grams active ingredient per hectare CHEAL =Chenopodium album L. (common lambsquarters) EPHHL = Euphorbiaheterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleafmorning-glory) KCHSC = Kochia scoparia (kochia) SORVU = Sorghum vulgare(grain sorghum) STEME = Stellaria media (chickweed) VIOTR = Violatricolor (wild pansy) ORYSA = Oryza sativa (common rice) TRZAW =Triticum aestivum (winter wheat)

TABLE 22 Effect (% visual injury) of compound 1 and bensulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Bensulfuron (g ai/ha) Application Rate0 17.5 17.5 BRSJU Obs 60 93 100 Exp 97 Δ 3 BRSNW Obs 50 70 93 Exp 85 Δ 8HELAN Obs 70 10 100 Exp 73 Δ 27 VIOTR Obs 5 0 10 Exp 5 Δ 5 ORYSA Obs 5 00 Exp 5 Δ −5 TRZAW Obs 5 0 10 Exp 5 Δ 5 g ae/ha = grams acid equivalentper hectare g ai/ha = grams active ingredient per hectare BRSJU =Brassica juncea (brown mustard) BRSNW = Brassica napus (winter rape)HELAN = Helianthus annuus (sunflower) VIOTR = Viola tricolor (wildpansy) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum(winter wheat)

TABLE 23 Effect (% visual injury) of compound 1 and chlorsulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Chlorsulfuron (g ai/ha) ApplicationRate 0 2.2 2.2 BRSNN Obs 70 93 100 Exp 98 Δ 2 CHEAL Obs 80 90 100 Exp 98Δ 2 CIRAR Obs 10 90 95 Exp 91 Δ 4 CYPES Obs 10 0 50 Exp 10 Δ 40 ECHCGObs 50 0 60 Exp 50 Δ 10 VIOTR Obs 30 60 75 Exp 72 Δ 3 KCHSC Obs 65 50 85Exp 83 Δ 3 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 5 0 0 Exp 5 Δ −5 g ae/ha= grams acid equivalent per hectare g ai/ha = grams active ingredientper hectare BRSNN = Brassica napus (spring rape) CHEAL = Chenopodiumalbum L. (common lambsquarters) CIRAR = Cirsium arvense (thistle) CYPES= Cyperus esculentus (nutsedge) ECHCG = Echinochloa crus-galli(barnyardgrass) VIOTR = Viola tricolor (wild pansy) KCHSC = Kochiascoparia (kochia) ORYSA = Oryza sativa (common rice) TRZAW = Triticumaestivum (winter wheat)

TABLE 24 Effect (% visual injury) of compound 1 and ethoxysulfuron onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Ethoxysulfuron(g ai/ha) 0 0 10 10 10 AMARE Obs 75 97 20 97 97 Exp 80 98 Δ 17 −1 KCHSCObs 60 60 0 65 65 Exp 60 60 Δ 5 5 STEME Obs 70 70 10 40 90 Exp 73 73 Δ−33 17 VIOTR Obs 5 10 40 50 55 Exp 43 46 Δ 7 9 ORYSA Obs 0 10 5 0 0 Exp5 15 Δ −5 −15 TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 ZEAMX Obs 0 0 0 0 0 Exp0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare g ai/ha = gramsactive ingredient per hectare AMARE = Amaranthus retroflexus (pigweed)KCHSC = Kochia scoparia (kochia) STEME = Stellaria media (chickweed)VIOTR = Viola tricolor (wild pansy) ORYSA = Oryza sativa (common rice)TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 25 Effect (% visual injury) of compound 1 and foramsulfuron onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Foramsulfuron(g ai/ha) 0 0 10 10 10 ALOMY Obs 0 0 93 100 95 Exp 93 93 Δ 7 2 AMARE Obs75 97 85 100 90 Exp 96 100 Δ 4 −10 ORYSA Obs 0 10 70 75 70 Exp 70 73 Δ 5−3 TRZAW Obs 0 0 97 97 97 Exp 97 97 Δ 0 0 ZEAMX Obs 0 0 0 0 0 Exp 0 0 Δ0 0 g ae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare ALOMY = Alopecurus myosuroides (blackgrass) AMARE= Amaranthus retroflexus (pigweed) ORYSA = Oryza sativa (common rice)TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 26 Effect (% visual injury) of compound 1 and flupyrsulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Flupyrsulfuron (g ai/ha) ApplicationRate 0 5 5 ABUTH Obs 70 80 97 Exp 94 Δ 3 CIRAR Obs 10 75 95 Exp 78 Δ 18CYPES Obs 10 70 85 Exp 73 Δ 12 KCHSC Obs 65 10 95 Exp 69 Δ 27 ORYSA Obs0 0 0 Exp 0 Δ 0 TRZAW Obs 5 0 5 Exp 5 Δ 0 g ae/ha = grams acidequivalent per hectare g ai/ha = grams active ingredient per hectareABUTH = Abutilon theophrasti (velvetleaf) CIRAR = Cirsium arvense(thistle) CYPES = Cyperus esculentus (nutsedge) KCHSC = Kochia scoparia(kochia) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum(winter wheat)

TABLE 27 Effect (% visual injury) of compound 1 and halosulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Halosulfuron (g ai/ha) ApplicationRate 0 8.75 8.75 CIRAR Obs 10 10 60 Exp 19 Δ 41 POLCO Obs 65 30 93 Exp76 Δ 18 ORYSA Obs 5 0 0 Exp 5 Δ −5 TRZAW Obs 5 0 0 Exp 5 Δ −5 ZEAMX Obs0 0 0 Exp 0 Δ 0 g ae/ha = grams acid equivalent per hectare g ai/ha =grams active ingredient per hectare CIRAR = Cirsium arvense (thistle)ORYSA = Oryza sativa (common rice) POLCO = Polygonum convolvulus (wildbuckwheat) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays(maize)

TABLE 28 Effect (% visual injury) of compound 1 and halosulfuron onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Halosulfuron (gai/ha) 0 0 17.5 17.5 17.5 AMARE Obs 75 97 30 97 100 Exp 83 98 Δ 15 2IPOHE Obs 10 10 20 40 70 Exp 28 28 Δ 12 42 KCHSC Obs 60 60 0 70 80 Exp60 60 Δ 10 20 STEME Obs 70 70 50 40 100 Exp 85 85 Δ −45 15 ORYSA Obs 010 0 0 10 Exp 0 10 Δ 0 0 TRZAW Obs 0 0 0 10 0 Exp 0 0 Δ 10 0 ZEAMX Obs 00 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare gai/ha = grams active ingredient per hectare AMARE = Amaranthusretroflexus (pigweed) IPOHE = Ipomoea hederacea (ivyleaf morning-glory)KCHSC = Kochia scoparia (kochia) STEME = Stellaria media (chickweed)ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winterwheat) ZEAMX = Zea mays (maize)

TABLE 29 Effect (% visual injury) of compound 1 and iodosulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Iodosulfuron (g ai/ha) ApplicationRate 0 2.5 2.5 POLCO Obs 75  80  100 Exp — — 94 Δ 6 TRZAW Obs 5 0 0 Exp— — 5 Δ −5 ZEAMX Obs 0 0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalentper hectare g ai/ha = grams active ingredient per hectare POLCO =Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winterwheat) ZEAMX = Zea mays (maize)

TABLE 30 Effect (% visual injury) of compound 1 and mesosulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Mesosulfuron (g ai/ha) ApplicationRate 0 3 3 KCHSC Obs 65 10 85 Exp 69 Δ 17 POLCO Obs 70 20 100 Exp 76 Δ24 SORVU Obs 10 97 100 Exp 97 Δ 3 ORYSA Obs 0 10 10 Exp 10 Δ 0 TRZAW Obs5 0 10 Exp 5 Δ 5 g ae/ha = grams acid equivalent per hectare g ai/ha =grams active ingredient per hectare KCHSC = Kochia scoparia (kochia)POLCO = Polygonum convolvulus (wild buckwheat) SORVU = Sorghum vulgare(grain sorghum) ORYSA = Oryza sativa (common rice) TRZAW = Triticumaestivum (winter wheat)

TABLE 31 Effect (% visual injury) of compound 1 and mesosulfuron +iodosulfuron on weeds. Compound 1 (g ae/ha) 5 0 5 Mesosulfuron +Iodosulfuron (g ai/ha) Application Rate 0 2.5 2.5 CIRAR Obs 10 93 97 Exp94 Δ 3 STEME Obs 50 70 90 Exp 85 Δ 5 ORYSA Obs 0 10 0 Exp 10 Δ −10 TRZAWObs 5 5 0 Exp 10 Δ −10 g ae/ha = grams acid equivalent per hectare gai/ha = grams active ingredient per hectare CIRAR = Cirsium arvense(thistle) STEME = Stellaria media (chickweed) ORYSA = Oryza sativa(common rice) TRZAW = Triticum aestivum (winter wheat)

TABLE 32 Effect (% visual injury) of compound 1 and metsulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Metsulfuron (g ai/ha) Application Rate0 1.5 1.5 CIRAR Obs 10 90 97 Exp 91 Δ 6 CYPES Obs 10 50 70 Exp 55 Δ 15ECHCG Obs 50 0 60 Exp 50 Δ 10 KCHSC Obs 65 70 93 Exp 90 Δ 4 ORYSA Obs 020 10 Exp 20 Δ −10 TRZAW Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acidequivalent per hectare g ai/ha = grams active ingredient per hectareCIRAR = Cirsium arvense (thistle) CYPES = Cyperus esculentus (nutsedge)ECHCG = Echinochloa crus-galli (barnyardgrass) KCHSC = Kochia scoparia(kochia) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum(winter wheat)

TABLE 33 Effect (% visual injury) of compound 1 and nicosulfuron onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Nicosulfuron (gai/ha) 0 0 17.5 17.5 17.5 BRSNW Obs 40 45 85 93 97 Exp 91 92 Δ 2 5 IPOHEObs 10 10 30 95 100 Exp 37 37 Δ 58 63 KCHSC Obs 60 60 5 65 70 Exp 62 62Δ 3 8 SETFA Obs 10 50 80 100 90 Exp 82 90 Δ 18 0 STEME Obs 70 70 30 3095 Exp 79 79 Δ −49 16 VIOTR Obs 5 10 40 50 30 Exp 43 46 Δ 7 −16 ZEAMXObs 0 0 0 0 5 Exp 0 0 Δ 0 5 g ae/ha = grams acid equivalent per hectareg ai/ha = grams active ingredient per hectare BRSNW = Brassica napus(winter rape) IPOHE = Ipomoea hederacea (ivyleaf morning-glory) KCHSC =Kochia scoparia (kochia) SETFA = Setaria faberi (giant foxtail) STEME =Stellaria media (chickweed) VIOTR = Viola tricolor (wild pansy) ZEAMX =Zea mays (maize)

TABLE 34 Effect (% visual injury) of compound 1 and orthosulfamuron onweeds. Application Rate Compound 1 (g ae/ha) 5 10 0 5 10 Orthosulfamuron(g ai/ha) 0 0 15 15 15 AMARE Obs 75 97 10 90 100 Exp 78 97 Δ 13 3 IPOHEObs 10 10 90 93 100 Exp 91 91 Δ 2 9 KCHSC Obs 60 60 0 65 73 Exp 60 60 Δ5 13 ORYSA Obs 0 10 0 0 0 Exp 0 10 Δ 0 −10 TRZAW Obs 0 0 0 5 5 Exp 0 0 Δ5 5 g ae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare AMARE = Amaranthus retroflexus (pigweed) IPOHE =Ipomoea hederacea (ivyleaf morning-glory) KCHSC = Kochia scoparia(kochia) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum(winter wheat)

TABLE 35 Effect (% visual injury) of compound 1 and sulfosulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Sulfosulfuron (g ai/ha) ApplicationRate 0 8.75 8.75 CIRAR Obs 10 85 90 Exp 87 Δ 4 CYPES Obs 10 80 85 Exp 82Δ 3 POLCO Obs 70 80 100 Exp 94 Δ 6 VIOTR Obs 30 80 95 Exp 86 Δ 9 ORYSAObs 0 10 0 Exp 10 Δ −10 TRZAW Obs 5 0 0 Exp 5 Δ −5 ZEAMX Obs 0 0 10 Exp0 Δ 10 g ae/ha = grams acid equivalent per hectare g ai/ha = gramsactive ingredient per hectare CIRAR = Cirsium arvense (thistle) CYPES =Cyperus esculentus (nutsedge) POLCO = Polygonum convolvulus (wildbuckwheat) VIOTR = Viola tricolor (wild pansy) ORYSA = Oryza sativa(common rice) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays(maize)

TABLE 36 Effect (% visual injury) of compound 1 and thifensulfuron onweeds. Compound 1 (g ae/ha) 5 0 5 Thifensulfuron (g ai/ha) ApplicationRate 0 15 15 CIRAR Obs 10 10 75 Exp 19 Δ 56 CYPES Obs 10 0 60 Exp 10 Δ50 ECHCG Obs 50 10 60 Exp 55 Δ 5 IPOHE Obs 30 85 100 Exp 90 Δ 11 ORYSAObs 0 10 10 Exp 10 Δ 0 TRZAW Obs 5 0 0 Exp 5 Δ −5 ZEAMX Obs 0 0 0 Exp 0Δ 0 g ae/ha = grams acid equivalent per hectare g ai/ha = grams activeingredient per hectare CIRAR = Cirsium arvense (thistle) CYPES = Cyperusesculentus (nutsedge) ECHCG = Echinochloa crus-galli (barnyardgrass)IPOHE = Ipomoea hederacea (ivyleaf morning-glory) ORYSA = Oryza sativa(common rice) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays(maize)

TABLE 37 Effect (% visual injury) of compound 1 and thifensulfuron +tribenuron on weeds. Compound 1 (g ae/ha) 5 0 5 Thifensulfuron +Tribenuron (g ai/ha) Application Rate 0 15 15 CYPES Obs 10 0 60 Exp 10 Δ50 KCHSC Obs 65 50 97 Exp 83 Δ 15 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 50 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare g ai/ha =grams active ingredient per hectare CYPES = Cyperus esculentus(nutsedge) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (commonrice) TRZAW = Triticum aestivum (winter wheat)

TABLE 38 Effect (% visual injury) of compound 1 and tribenuron on weeds.Compound 1 (g ae/ha) 5 0 5 Tribenuron (g ai/ha) Application Rate 0 7.57.5 CYPES Obs 10 0 70 Exp 10 Δ 60 IPOHE Obs 30 65 100 Exp 76 Δ 25 KCHSCObs 65 70 100 Exp 90 Δ 11 POLCO Obs 70 90 100 Exp 97 Δ 3 ORYSA Obs 0 100 Exp 10 Δ −10 TRZAW Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acidequivalent per hectare g ai/ha = grams active ingredient per hectareCYPES = Cyperus esculentus (nutsedge) IPOHE = Ipomoea hederacea (ivyleafmorning-glory) KCHSC = Kochia scoparia (kochia) POLCO = Polygonumconvolvulus (wild buckwheat) ORYSA = Oryza sativa (common rice) TRZAW =Triticum aestivum (winter wheat)

The compositions and methods of the appended claims are not limited inscope by the specific compositions and methods described herein, whichare intended as illustrations of a few aspects of the claims and anycompositions and methods that are functionally equivalent are intendedto fall within the scope of the claims. Various modifications of thecompositions and methods in addition to those shown and described hereinare intended to fall within the scope of the appended claims. Further,while only certain representative compositions and method stepsdisclosed herein are specifically described, other combinations of thecompositions and method steps also are intended to fall within the scopeof the appended claims, even if not specifically recited. Thus, acombination of steps, elements, components, or constituents may beexplicitly mentioned herein or less, however, other combinations ofsteps, elements, components, and constituents are included, even thoughnot explicitly stated. The term “comprising” and variations thereof asused herein is used synonymously with the term “including” andvariations thereof and are open, non-limiting terms. Although the terms“comprising” and “including” have been used herein to describe variousembodiments, the terms “consisting essentially of” and “consisting of”can be used in place of “comprising” and “including” to provide for morespecific embodiments of the invention and are also disclosed. Other thanin the examples, or where otherwise noted, all numbers expressingquantities of ingredients, reaction conditions, and so forth used in thespecification and claims are to be understood at the very least, and notas an attempt to limit the application of the doctrine of equivalents tothe scope of the claims, to be construed in light of the number ofsignificant digits and ordinary rounding approaches.

1. A herbicidal composition comprising a herbicidally effective amountof (a) a pyridine carboxylic acid herbicide or an agriculturallyacceptable N-oxide, salt, or ester thereof, and (b) an acetolactatesynthase (ALS) inhibitor or an agriculturally acceptable salt or esterthereof, wherein the weight ratio of (a) in grams acid equivalent (g ae)to (b) in grams active ingredient (g ai) is from 1:400 to 10:1, whereinthe pyridine carboxylic acid herbicide comprises a compound defined byFormula (I)

wherein X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio; R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) ishydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) areindependently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring; A is one of groupsA1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN; R⁶, R^(6′), and R^(6″), if applicable to theA group, are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄haloalkylamino, OH, CN, or NO₂; R⁷ and R^(7′) are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino, C₁-C₄ haloalkylamino, or phenyl; R⁸ is hydrogen, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆trialkylsilyl, or phenyl; or an agriculturally acceptable N-oxide orsalt thereof.
 2. The composition of claim 1, wherein the pyridinecarboxylic acid herbicide comprises a compound defined by Formula (II)

wherein R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) is hydrogen,C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1′″) areindependently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3,A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18,A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32,A33, A34, A35, or A36; R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, OH, or CN; R⁶, R^(6′), and R^(6″) are independentlyhydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl,halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino,C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂; R⁷ and R^(7′)are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl,cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl;and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆trialkylsilyl, or phenyl; or an agriculturallyacceptable N-oxide or salt thereof.
 3. The composition of claim 2,wherein R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, orC₇-C₁₀ arylalkyl; R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl,C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, or C₁-C₄ haloalkylthio; R³ and R⁴ arehydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, or R³ and R⁴ taken together represent═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen,C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆alkylamino; A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15,A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32; R⁵ is hydrogen,halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl,C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino; R⁶,R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl,amino or C₁-C₄ alkylamino; and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, or C₁-C₆alkylcarbamyl.
 4. The composition of claim 1, wherein the pyridinecarboxylic acid herbicide comprises a compound defined by Formula (III):

wherein X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃haloalkylthio; R¹ is OR^(1′) or NR^(1″)R^(1′″), wherein R^(1′) ishydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(′″) areindependently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl,cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ ishydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ andR⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ andR⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′)are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl,C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken togetherwith ═C represent a 5- or 6-membered saturated ring; R⁶ and R^(6′) areindependently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl,cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN,or NO₂; R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄haloalkylamino, or phenyl; and R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl,C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, orphenyl; or an agriculturally acceptable N-oxide or salt thereof.
 5. Thecomposition of claim 1, wherein the pyridine carboxylic acid herbicidecomprises one of the following:


6. The composition of claim 1, wherein the pyridine carboxylic acidherbicide comprises


7. The composition of claim 1, wherein (b) comprises atriazolopyrimidine sulfonamide herbicide.
 8. The composition of claim 7,wherein the triazolopyrimidine sulfonamide herbicide is selected fromthe group consisting of florasulam, cloransulam, diclosulam,flumetsulam, metosulam, penoxsulam, pyroxsulam, agriculturallyacceptable salts and esters thereof, and combinations thereof.
 9. Thecomposition of claim 8, wherein the weight ratio of (a) to (b) is from1:10 to 10:1.
 10. (canceled)
 11. (canceled)
 12. The composition of claim1, wherein (b) is an imidazolinone herbicide.
 13. The composition ofclaim 12, wherein the imidazolinone herbicide is selected from the groupconsisting of imazamethabenz, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, agriculturally acceptable salts and esters thereof, andcombinations thereof.
 14. The composition of claim 13, wherein theweight ratio of (a) to (b) is from 1:50 to 10:1.
 15. (canceled) 16.(canceled)
 17. The composition of claim 1, wherein (b) is a pyrimidinyloxybenzoate herbicide.
 18. The composition of claim 17, wherein thepyrimidinyl oxybenzoate herbicide is selected from the group consistingof bispyribac, pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan,pyrithiobac, agriculturally acceptable salts and esters thereof, andcombinations thereof.
 19. (canceled)
 20. (canceled)
 21. The compositionof claim 18, wherein the weight ratio of (a) to (b) is from 1:10 to 5:1.22. The composition of claim 1, wherein (b) is a sulfonylaminocarbonyltriazolinone herbicide.
 23. The composition of claim 22, wherein thesulfonylaminocarbonyl triazolinone herbicide is selected from the groupconsisting of flucarbazone, propoxycarbazone, thiencarbazone,agriculturally acceptable salts and esters thereof, and combinationsthereof.
 24. (canceled)
 25. (canceled)
 26. The composition of claim 23,wherein the weight ratio of (a) to (b) is from 1:10 to 5:1
 27. Thecomposition of claim 1, wherein (b) is a sulfonylurea herbicide.
 28. Thecomposition of claim 27, wherein the sulfonylurea herbicide is selectedfrom the group consisting of amidosulfuron, azimsulfuron, bensulfuron,chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron,ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron,flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron,iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,propyrisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron,sulfosulfuron, triasulfuron, tribenuron, thifensulfuron,trifloxysulfuron, triflusulfuron, tritosulfuron, agriculturallyacceptable salts and esters thereof, and combinations thereof.
 29. Thecomposition of claim 28, wherein the weight ratio of (a) to (b) is from1:20 to 5:1.
 30. (canceled)
 31. (canceled)
 32. The composition of claim1, further comprising an agriculturally acceptable adjuvant or carrier.33. The composition of claim 1, further comprising an additionalpesticide.
 34. The composition of claim 1, wherein the activeingredients in the composition consist of (a) and (b).
 35. (canceled)36. The composition of claim 1, wherein the composition is provided as aherbicidal concentrate.
 37. A method of controlling undesirablevegetation comprising applying to vegetation or an area adjacent thevegetation or applying to soil or water to control the emergence orgrowth of vegetation a herbicidally effective amount of the compositionof claim
 1. 38-67. (canceled)
 68. The method of claim 37, wherein (a) isapplied in amount of from 0.1 g ae/ha to 300 g ae/ha.
 69. (canceled) 70.The method of claim 37, wherein (b) is applied in amount of from 0.25 gai/ha to 1700 g ai/ha.
 71. (canceled)
 72. (canceled)
 73. The method ofclaim 37, wherein (a) and (b) are applied post-emergence to theundesirable vegetation.
 74. (canceled)
 75. (canceled)
 76. The method ofclaim 37, further comprising applying an additional pesticide. 77.(canceled)
 78. (canceled)
 79. The method of claim 37, wherein theundesirable vegetation includes a broadleaf weed.
 80. The method ofclaim 37, wherein the undesirable vegetation comprises a herbicideresistant or tolerant weed.
 81. (canceled)
 82. (canceled)
 83. The methodof claim 37, wherein the undesirable vegetation includes velvetleaf,blackgrass, pigweed, wild oat, brown mustard, rutabaga, spring rape,winter rape, turnip, lambsquarters, thistle, nutsedge, large crabgrass,barnyardgrass, poinsettia, soybean, sunflower, ivyleaf morning-glory,kochia, wild buckwheat, giant foxtail, sorghum, common chickweed, wildpansy, or a combination thereof.
 84. The method of claim 37, wherein theactive ingredients applied to the vegetation or an area adjacent thevegetation or applied to soil or water to control the emergence orgrowth of vegetation consist of (a) and (b).